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  ASYMMETRIC-SYNTHESIS OF BICYCLIC AMINO-ACID DERIVATIVES BY AZA-DIELS-ALDER REACTIONS IN AQUEOUS-SOLUTION

Waldmann, H., & BRAUN, M. (1991). ASYMMETRIC-SYNTHESIS OF BICYCLIC AMINO-ACID DERIVATIVES BY AZA-DIELS-ALDER REACTIONS IN AQUEOUS-SOLUTION. LIEBIGS ANNALEN DER CHEMIE, (10), 1045-1048.

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 Creators:
Waldmann, Herbert1, Author           
BRAUN, M2, Author
Affiliations:
1Abt. IV: Chemische Biologie, Max Planck Institute of Molecular Physiology, Max Planck Society, ou_1753290              
2external, ou_persistent22              

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Free keywords: CHIRAL AUXILIARIES; STEREOSELECTIVE SYNTHESIS; ESTERS; CYCLOPENTADIENE; CYCLOADDITIONS; ASYMMETRIC SYNTHESIS; AZA-DIELS-ALDER REACTION; AMINO ACIDS
 Abstract: Derivatives 7-10 and 13-16 of methyl and ethyl 2-azabicyclo[2.2.1]heptane-3-carboxylates are synthesized by Aza-Diels-Alder reactions of chiral iminium ions, formed in situ from glyoxylic acid and chiral amines, with cyclopentadiene. Whereas the heterodienophiles derived from phenylglycinol and esters of sterically more demanding amino acids fail to undergo asymmetric cycloadditions, with alanine methyl ester and (R)-1-phenylethylamine hydrochloride the cycloadducts are formed in yields of 15 and 52%, respectively, reaching de values of up to 90:10 for the exo isomers.

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Language(s): eng - English
 Dates: 1991-10
 Publication Status: Issued
 Pages: 4
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: ISI: A1991GN36800011
 Degree: -

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Title: LIEBIGS ANNALEN DER CHEMIE
Source Genre: Journal
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Affiliations:
Publ. Info: Weinheim : VCH
Pages: - Volume / Issue: (10) Sequence Number: - Start / End Page: 1045 - 1048 Identifier: ISSN: 0170-2041