Chemistry of Aziridine Carboxylic Acids, 7 . Synthesis of Ethyl (2 R ,3 S )‐ N ‐Boc‐ and ‐ N ‐Benzyl‐3‐vinylaziridine‐2‐carboxylates: New Potential Building Blocks for Enantiomerically Pure Unsaturated Amino Acids | Zendy

Jähnisch Klaus | Zendy

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Chemistry of Aziridine Carboxylic Acids, 7 . Synthesis of Ethyl (2 R ,3 S )‐ N ‐Boc‐ and ‐ N ‐Benzyl‐3‐vinylaziridine‐2‐carboxylates: New Potential Building Blocks for Enantiomerically Pure Unsaturated Amino Acids

Author(s) -

Jähnisch Klaus

Publication year - 1997

Publication title -

liebigs annalen

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 0947-3440

DOI - 10.1002/jlac.199719970419

Subject(s) - aziridine , chemistry , carboxylic acid , ammonia , selectivity , organic chemistry , medicinal chemistry , stereochemistry , ring (chemistry) , catalysis

Enantiomerically pure cis ‐ and trans ‐1 H ‐aziridine‐carboxylic acid derivatives 2a, b and 3a, b have been prepared by asymmetric Michael‐type addition of ammonia to chiral acrylates 1a, b with high syn selectivity. The title compounds were obtained from the diols 8a, b by Corey‐Winter olefination.

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