Stereoselective Synthesis of Tetrasubstituted Olefins through a Halogen‐Induced 1,2‐Silyl Migration | Zendy

Barczak Nicholas T. | Zendy; Rooke Douglas A. | Zendy; Menard Zachary A. | Zendy; Ferreira Eric M. | Zendy

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Stereoselective Synthesis of Tetrasubstituted Olefins through a Halogen‐Induced 1,2‐Silyl Migration

Author(s) -

Barczak Nicholas T.,

Rooke Douglas A.,

Menard Zachary A.,

Ferreira Eric M.

Publication year - 2013

Publication title -

angewandte chemie international edition

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 1433-7851

DOI - 10.1002/anie.201303007

Subject(s) - silylation , stereoselectivity , electrophile , alkyne , halogen , carbon skeleton , chemistry , computer science , world wide web , stereochemistry , organic chemistry , catalysis , alkyl

Migrating through Si valley : The highly stereoselective formation of α‐silyl‐β‐ haloenones by way of silicon group migration is described. Electrophilic activation of the alkyne by N ‐halosuccinimides induced an anti ‐selective migration to give highly substituted enones (see scheme). These enone products can be readily converted to the all‐carbon tetrasubstituted alkenes while maintaining their geometry.

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