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

Chowdhury Raghunath | Zendy; Ghosh Sunil K. | Zendy

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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

Author(s) -

Chowdhury Raghunath,

Ghosh Sunil K.

Publication year - 2008

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.200800385

Subject(s) - chemistry , phosphonate , domino , stereoselectivity , aldehyde , ylide , lithium (medication) , cascade reaction , organic chemistry , base (topology) , medicinal chemistry , catalysis , medicine , mathematical analysis , mathematics , endocrinology

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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