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Sequential Double Olefination of 2-(Arylmethylidene)-2-phosphonoacetonitrile with Dimsyl Lithium and Aldehydes: A Domino Route to Densely Substituted 1,3-Butadienes

✍ Scribed by Raghunath Chowdhury; Sunil K. Ghosh

Publisher: John Wiley and Sons
Year: 2008
Tongue: English
Weight: 195 KB
Volume: 2008
Category: Article
ISSN: 1434-193X
DOI: 10.1002/ejoc.200800385

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✦ Synopsis

Abstract

An efficient and highly stereoselective synthesis of densely substituted 1,3‐dienes has been achieved which entails a sequential double olefination of 2‐(arylmethylidene)‐2‐phosphonoacetonitriles by a one‐pot domino process involving Michael addition of dimsyllithium to 2‐(arylmethylidene)‐2‐phosphonoacetonitrile, Horner–Wadsworth–Emmons reaction of the resulting phosphonate ylide with the added aldehyde followed by base induced methylsulfenoxy elimination. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

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ChemInform Abstract: Sequential Double O

ChemInform Abstract: Sequential Double Olefination of 2-(Arylmethylidene)-2-phosphonoacetonitrile with Dimsyl Lithium and Aldehydes: A Domino Route to Densely Substituted 1,3-Butadienes.

✍ Raghunath Chowdhury; Sunil K. Ghosh 📂 Article 📅 2008 🏛 John Wiley and Sons ⚖ 32 KB 👁 1 views

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