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Catalytic, Enantioselective Ring Opening of Aziridines

✍ Scribed by Christoph Schneider

Publisher
John Wiley and Sons
Year
2009
Tongue
English
Weight
347 KB
Volume
48
Category
Article
ISSN
0044-8249

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✦ Synopsis

Abstract

Cooperative metal centers in a bimetallic catalyst facilitate the highly enantioselective ring opening of meso aziridines 1 with silyl nucleophiles (see scheme; TMS=trimethylsilyl). The 1,2‐azidoamides 2 and 1,2‐amidonitriles 3 obtained in this way in high yields and with up to 99 %β€…ee are valuable precursors to enantiomerically pure 1,2‐diamines and β‐amino acids.magnified image

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Nucleophilic ring opening of aziridines
Nucleophilic ring opening of aziridines
✍ Helmut Stamm πŸ“‚ Article πŸ“… 1999 πŸ› John Wiley and Sons 🌐 English βš– 139 KB πŸ‘ 1 views

This account of research work on nucleophilic ring opening (NRO) of aziridines (Az's) demonstrates the broad synthetic scope of this reaction, inclusive secondary reactions, and it discusses the special mechanistic fundamentals and details as well as mechanistic variants. Formation of a C-C bond by