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Selective synthesis ofE-isomers of aldoximes via a domino aza-Michael/retro-Michael reaction

✍ Scribed by Wei Chen; Wei-Guo Yu; Hai-Bo Shi; Xiao-Yan Lu

Book ID
115063856
Publisher
Versita
Year
2012
Tongue
English
Weight
154 KB
Volume
66
Category
Article
ISSN
0366-6352

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✦ Synopsis

Abstract

A highly stereoselective synthesis of E-isomer of aldoximes was developed through a base-catalysed domino aza-Michael/retro-Michael reaction of hydroxylamine and 2-(R-benzylidene)malononitrile. This reaction generates (E)-aldoxime diastereomer in high yields (eight examples, isolated yields of 82-93 %), excellent diastereomeric purity (diastereomeric ratio higher than 95: 5 by 1H NMR), and proceeds under mild reaction conditions (aqueous NaOH, pH 12, room temperature, 4 h).

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Asymmetric Synthesis of Polyfunctionalized Pyrrolidines via a Thiourea Catalyzed Domino Mannich/Aza-Michael Reaction
✍ Dieter Enders; Dominik P. Göddertz; Christian Beceño; Gerhard Raabe 📂 Article 📅 2010 🏛 John Wiley and Sons 🌐 English ⚖ 230 KB 👁 2 views

## Abstract The domino Mannich/aza‐Michael reaction of γ‐malonate‐substituted α,β‐unsaturated esters with __N__‐protected arylaldimines has been achieved. Catalyzed by bifunctional thioureas, 2,5‐__cis__‐configured polysubstituted pyrrolidines are obtained in good to excellent yields (76–99%), enan