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Scientific article
French

A Mild and Efficient CH2-Extrusion Reaction for the Enantiospecific Synthesis of Highly Configurationally Stable Tröger Bases

Published inAngewandte Chemie, vol. 54, no. 26, p. 7520-7523
Publication date2015
Abstract

A novel CH2-extrusion reaction leading to the transformation of ethano-Tröger bases into disubstituted methano derivatives is reported (yields up to 93 %). Under mild and metal-free oxidative conditions, a loss of CH2 and a ring contraction are provoked. Despite two bond cleavages at stereogenic nitrogen and carbon centers and a temporary rupture of the bicyclic structure, a very high enantiospecificity (es≥98 %) is observed for this unusual reaction.

Keywords
  • Configuration determination
  • Enantioselectivity
  • Heterocycles
  • Ring contraction
  • Stereochemistry
Citation (ISO format)
PUJARI, Sandip A. et al. A Mild and Efficient CH2-Extrusion Reaction for the Enantiospecific Synthesis of Highly Configurationally Stable Tröger Bases. In: Angewandte Chemie, 2015, vol. 54, n° 26, p. 7520–7523. doi: 10.1002/anie.201500435
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Article (Published version)
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Identifiers
ISSN of the journal1433-7851
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Technical informations

Creation06/19/2015 8:07:00 AM
First validation06/19/2015 8:07:00 AM
Update time03/14/2023 11:22:54 PM
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