Unified Approach to Fused and Spirocyclic Oxindoles through Lewis‐Acid‐Promoted Opening of Spiroepoxyoxindoles with Allylsilanes: Application to the Formal Synthesis of (±)‐Physovenine | Zendy

Sharma Brijesh M. | Zendy; Yadav Mahesh | Zendy; Gonnade Rajesh G. | Zendy; Kumar Pradeep | Zendy

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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.

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