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Unified Approach to Fused and Spirocyclic Oxindoles through Lewis‐Acid‐Promoted Opening of Spiroepoxyoxindoles with Allylsilanes: Application to the Formal Synthesis of (±)‐Physovenine
Author(s) -
Sharma Brijesh M.,
Yadav Mahesh,
Gonnade Rajesh G.,
Kumar Pradeep
Publication year - 2017
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.201700259
Subject(s) - chemistry , regioselectivity , lewis acids and bases , quaternary carbon , formal synthesis , combinatorial chemistry , catalysis , stereochemistry , organic chemistry , enantioselective synthesis
A protocol for the construction of oxindoles containing all‐carbon quaternary centres in a highly regioselective manner has been developed. The reaction involves opening of spiroepoxyoxindoles with allylsilanes to give Hosomi–Sakurai‐type products as well as new silicon‐containing spirocyclic oxindoles. A formal synthesis of (±)‐physovenine was accomplished in five steps using this protocol.