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  ASYMMETRIC AZA DIELS-ALDER REACTIONS OF AMINO-ACID ESTER IMINES WITH BRASSARD-DIENE

Waldmann, H., BRAUN, M., & DRAGER, M. (1991). ASYMMETRIC AZA DIELS-ALDER REACTIONS OF AMINO-ACID ESTER IMINES WITH BRASSARD-DIENE. TETRAHEDRON-ASYMMETRY, 2(12), 1231-1246. doi:10.1016/S0957-4166(00)80023-3.

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 Creators:
Waldmann, Herbert1, Author           
BRAUN, M2, Author
DRAGER, 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: (S)-PROLINE BENZYL ESTER; CHIRAL AUXILIARIES; AQUEOUS-SOLUTION; CYCLOCONDENSATION REACTION; CYCLOADDITIONS; PIPERIDINE; ALKALOIDS; SCOPE
 Abstract: Imines 1 obtained from aromatic, aliphatic or functionalized aldehydes and valine tert-butyl ester undergo Lewis acid catalyzed hetero Diels-Alder reactions with Brassard's diene 2. The cycloadducts are formed in good to high yields and with diastereomer ratios of 92:8-97:3. For the removal of the chiral auxiliary group a new method was developed whose principle consists in the conversion of the amino acid alpha-C-atom into an acetalic center employing a Curtius rearrangement as the key step.

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Language(s): eng - English
 Dates: 1991
 Publication Status: Published in print
 Pages: 16
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Degree: -

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Title: TETRAHEDRON-ASYMMETRY
Source Genre: Journal
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Publ. Info: KIDLINGTON, OXFORD : PERGAMON-ELSEVIER SCIENCE
Pages: - Volume / Issue: 2 (12) Sequence Number: - Start / End Page: 1231 - 1246 Identifier: ISSN: 0957-4166