2003-06-01, English, Article, Journal or magazine article edition: Photo aldol reactions with 5-methoxyoxazoles: highly regio- and diastereoselective synthesis of [alpha]-amino [beta]-hydroxy carboxylic acid derivatives.(Author Abstract) Griesbeck, Axel G.; Bondock, Samir

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Physical Description
  • Author Abstract
  • Magazine/​Journal article
Published
  • NRC Research Press, 2003 June
Language
  • English

Edition details

Title
  • Photo aldol reactions with 5-methoxyoxazoles: highly regio- and diastereoselective synthesis of [alpha]-amino [beta]-hydroxy carboxylic acid derivatives.(Author Abstract)
Also Titled
  • Photo aldol reactions with 5-methoxyoxazoles: highly regio- and diastereoselective synthesis of [alpha]-amino [beta]-hydroxy carboxylic acid derivatives.
Appears In
  • Canadian Journal of Chemistry, v.81, no.6, 2003 June, p.555(5) (ISSN: 0008-4042)
Author
  • Griesbeck, Axel G.
  • Bondock, Samir
Published
  • NRC Research Press, 2003 June
Physical Description
  • Author Abstract
  • Magazine/​Journal article
Subjects
Target Audience
  • Academic
Summary
  • A versatile route to derivatives of [alpha]-amino [beta]-hydroxy carboxylic acids, either with tertiary (from a corresponding glycine equivalent) or a quaternary [alpha]-carbon center is described. The key reaction is the cycloaddition of electronically excited carbonyl compounds (aromatic and aliphatic aldehydes, respectively) to oxazoles. To make the products hydrolytically more labile, a methoxy substituent at position C-5 was introduced leading to the formation of cycloadducts with an orthoester substructure. The photocycloaddition, either with triplet excited (aromatic) carbonyls or with singlet excited (aliphatic) carbonyls, led to the formation of mixtures of endo- and exo-diastereoisomers with moderate to very high exo-selectivities. The 4-unsubstituted 5-methoxyoxazole 1 (glycine equivalent) gave the [2 + 2]-adducts 3a-3f with aldehydes 2a-2f in high yields and excellent diastereoselectivities. Hydrolysis of these compounds resulted in the [alpha]-amino [beta]-hydroxy esters 4a-4f with preferred erythro (S*,S*) configuration. As an extension of this process, 4-alkylated 5-methoxyoxazoles 5a-5f were applied as alkene components and the corresponding cycloadducts with benzaldehyde 6a-6f were obtained. Again, the exo-diastereoisomers were formed as the major products in diastereoselectivities from 73:27 (exo:endo) up to [is greater than]95:5. Hydrolysis of these adducts resulted in the formation of [alpha]amino [beta]-hydroxy esters 7a-7f with like (S*,S*) configuration of the major diastereoisomers. Key words: photo aldol reaction, oxazoles, oxetanes, photocycloaddition, amino acids, hydroxy acids.
Terms of Use
  • COPYRIGHT 2003 NRC Research Press
Language
  • English
Database
  • Gale Academic OneFile
  • Gale General OneFile
  • Gale Expanded Academic
Identifier
  • 109178874

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Bialik College. Bialik College Library. Not open to the public Periodical; Journal, magazine, other English; French
CAVAL. CARM Centre. May not be open to the public brn.181082; Held; Vol. 52, no. 1 - v. 77; Jan. 1974 - 1999; Inc. Periodical; Journal, magazine, other English; French
Charles Sturt University. CSU Library - Electronic Resources (shared). Open to the public 000098168; Full Text Available; ProQuest Natural Science Journals New Platform - Available from 1998 until 2007 Periodical; Journal, magazine, other English; French
Cumberland Council. Auburn Library. Open to the public Periodical; Journal, magazine, other English; French
Defence Science and Technology Group. DST Group Research Information Services - Melbourne. Not open to the public Serials; Vol. 29-v.68; 1951-1990; incomplete Periodical; Journal, magazine, other English; French
Department of Agriculture and Fisheries Qld. Dept of Agriculture and Fisheries Qld Research Information Service. Not open to the public STACK; vol.29,no.1-v.31; 1951-1953 Periodical; Journal, magazine, other English; French
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Flinders University. Flinders University Central Library. Open to the public 9957369701771; 540.5 C21 Periodical; Journal, magazine, other English; French
James Cook University. Townsville Campus Library. Open to the public 104; <104>; Vol. 29 - v. 74; 1951 - 1996; Incomplete Periodical; Journal, magazine, other English; French
Macquarie University. Macquarie University Library. Open to the public 992055610802171; QD1 .C285; Vol. 29 (1951)-vol. 33 (1955); vol. 39 (1961)-vol. 83, no. 8 (2005); vol. 83, no. 10 (2005)-vol. 83, no. 12 (2005) Periodical; Journal, magazine, other English; French
Monash University. Monash University Library. Open to the public 99867301751; 540.5 C212; v. 29 (1951) to v.84 (2006) ; Incomplete ; Includes Indexes; Lacks: v. 52 (1974) ; v. 53, no. 1-6 (1975) ; v. 53, no. 13-24 (1975) ; v.54 (1976) to v. 55 (1977) ; v. 73 (1995) to v. 77 (1999); HA; XST-TE Periodical; Journal, magazine, other English; French
National Library of Australia. Open to the public 2333488; S 540.5 CAN; Vol. 29-v. 64 (1951-1986) Periodical; Journal, magazine, other English; French
NSW Department of Industry. DTIRIS: Electronic Resources Library. Not open to the public V 29 1951 - V 75 1997 Periodical; Journal, magazine, other English; French
RMIT University. RMIT University Library. Open to the public 9912892330001341; PER 540 C212; Incomplete. Held in Storage. Request from <a href=http://www.rmit.edu.au/library/dds target=_blank>Document Delivery</a>; v. 51, no. 1 (Jan. 1, 1973)-v. 70, no. 12 (Dec. 1992) Periodical; Journal, magazine, other English; French
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State Library of NSW. Open to the public Held; 1951-1991 Periodical; Journal, magazine, other English; French
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St Vincent's Hospital (Sydney). Walter McGrath Library. Not open to the public (EbpS)ebs515368; held Periodical; Journal, magazine, other English; French
The University of Melbourne. The University Library. Open to the public Ch P CANA; v.29-v.84; 1951-2006 Periodical; Journal, magazine, other English; French
The University of Sydney. University of Sydney Library. Open to the public .b1156507x; held Periodical; Journal, magazine, other English; French
University of Adelaide. Barr Smith Library. Open to the public 9996397001811; MICROFICHE PER 86; v.60(1982)-v.69(1991) Periodical; Journal, magazine, other English; French
University of Newcastle. University of Newcastle Library. Open to the public 540.5/9; Vol. 29, no. 1-v. 75, no. 12; Jan. 1951-Dec. 1997 Periodical; Journal, magazine, other English; French
University of New England. Dixson Library. Open to the public 1024-67060; <1024-67060>; P540.5/CAN <1024-67060>; V.29 (1951)- Periodical; Journal, magazine, other English; French
University of Tasmania. Open to the public .b10389556; Scien ser v29-74;1951-96 Periodical; Journal, magazine, other English
University of Western Australia. University of Western Australia Library. Open to the public 9944031702101; HELD; V. 76-92 ; 1998-2014; V. 49-75 ; 1971-1997 Periodical; Journal, magazine, other English; French
University of Wollongong. University of Wollongong Library. Open to the public Online access. Not available for document delivery Periodical; Journal, magazine, other English; French
Western Sydney University. Campbelltown Campus Library. Open to the public 399266; 540.5 4 Periodical; Journal, magazine, other English; French
Western Sydney University. Penrith Campus Library. Open to the public 399266; Online version Periodical; Journal, magazine, other English; French
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National Library of Australia. Open to the public 2333488; S 540.5 CAN; Vol. 29-v. 64 (1951-1986) Periodical; Journal, magazine, other English; French
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These 15 locations in New South Wales:

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Charles Sturt University. CSU Library - Electronic Resources (shared). Open to the public 000098168; Full Text Available; ProQuest Natural Science Journals New Platform - Available from 1998 until 2007 Periodical; Journal, magazine, other English; French
Cumberland Council. Auburn Library. Open to the public Periodical; Journal, magazine, other English; French
Macquarie University. Macquarie University Library. Open to the public 992055610802171; QD1 .C285; Vol. 29 (1951)-vol. 33 (1955); vol. 39 (1961)-vol. 83, no. 8 (2005); vol. 83, no. 10 (2005)-vol. 83, no. 12 (2005) Periodical; Journal, magazine, other English; French
NSW Department of Industry. DTIRIS: Electronic Resources Library. Not open to the public V 29 1951 - V 75 1997 Periodical; Journal, magazine, other English; French
Shellharbour City Council. Shellharbour City Library Service. Open to the public Periodical; Journal, magazine, other English; French
Shore School. Boer War Contingent Memorial Library. Not open to the public Periodical; Journal, magazine, other English; French
Southern Cross University. University Library Lismore. Open to the public Electronic resource - Check catalogue for holdings Periodical; Journal, magazine, other English; French
State Library of NSW. Open to the public Held; 1951-1991 Periodical; Journal, magazine, other English; French
St Vincent's Hospital (Sydney). Walter McGrath Library. Not open to the public (EbpS)ebs515368; held Periodical; Journal, magazine, other English; French
The University of Sydney. University of Sydney Library. Open to the public .b1156507x; held Periodical; Journal, magazine, other English; French
University of Newcastle. University of Newcastle Library. Open to the public 540.5/9; Vol. 29, no. 1-v. 75, no. 12; Jan. 1951-Dec. 1997 Periodical; Journal, magazine, other English; French
University of New England. Dixson Library. Open to the public 1024-67060; <1024-67060>; P540.5/CAN <1024-67060>; V.29 (1951)- Periodical; Journal, magazine, other English; French
University of Wollongong. University of Wollongong Library. Open to the public Online access. Not available for document delivery Periodical; Journal, magazine, other English; French
Western Sydney University. Campbelltown Campus Library. Open to the public 399266; 540.5 4 Periodical; Journal, magazine, other English; French
Western Sydney University. Penrith Campus Library. Open to the public 399266; Online version Periodical; Journal, magazine, other English; French
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Department of Agriculture and Fisheries Qld. Dept of Agriculture and Fisheries Qld Research Information Service. Not open to the public STACK; vol.29,no.1-v.31; 1951-1953 Periodical; Journal, magazine, other English; French
James Cook University. Townsville Campus Library. Open to the public 104; <104>; Vol. 29 - v. 74; 1951 - 1996; Incomplete Periodical; Journal, magazine, other English; French
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These 2 locations in South Australia:

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Flinders University. Flinders University Central Library. Open to the public 9957369701771; 540.5 C21 Periodical; Journal, magazine, other English; French
University of Adelaide. Barr Smith Library. Open to the public 9996397001811; MICROFICHE PER 86; v.60(1982)-v.69(1991) Periodical; Journal, magazine, other English; French
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Bialik College. Bialik College Library. Not open to the public Periodical; Journal, magazine, other English; French
CAVAL. CARM Centre. May not be open to the public brn.181082; Held; Vol. 52, no. 1 - v. 77; Jan. 1974 - 1999; Inc. Periodical; Journal, magazine, other English; French
Defence Science and Technology Group. DST Group Research Information Services - Melbourne. Not open to the public Serials; Vol. 29-v.68; 1951-1990; incomplete Periodical; Journal, magazine, other English; French
Monash University. Monash University Library. Open to the public 99867301751; 540.5 C212; v. 29 (1951) to v.84 (2006) ; Incomplete ; Includes Indexes; Lacks: v. 52 (1974) ; v. 53, no. 1-6 (1975) ; v. 53, no. 13-24 (1975) ; v.54 (1976) to v. 55 (1977) ; v. 73 (1995) to v. 77 (1999); HA; XST-TE Periodical; Journal, magazine, other English; French
RMIT University. RMIT University Library. Open to the public 9912892330001341; PER 540 C212; Incomplete. Held in Storage. Request from <a href=http://www.rmit.edu.au/library/dds target=_blank>Document Delivery</a>; v. 51, no. 1 (Jan. 1, 1973)-v. 70, no. 12 (Dec. 1992) Periodical; Journal, magazine, other English; French
The University of Melbourne. The University Library. Open to the public Ch P CANA; v.29-v.84; 1951-2006 Periodical; Journal, magazine, other English; French
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