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Ueno-Stork Cyclization

(Ueno-Stork Reaction, Ueno-Stork Radical Cyclization)

Published Online: 15 SEP 2010

DOI: 10.1002/9780470638859.conrr633

Comprehensive Organic Name Reactions and Reagents

Comprehensive Organic Name Reactions and Reagents

How to Cite

2010. Ueno-Stork Cyclization. Comprehensive Organic Name Reactions and Reagents. 633:2826–2829.

Publication History

  1. Published Online: 15 SEP 2010

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Abstract

This reaction is a radical cyclization of the α-haloacetal of an allylic alcohol with stereochemical control to form polysubstituted tetrahydrofuran and γ-lactone derivatives and is generally referred to as the Ueno–Stork reaction. It has been reported that the chiral center of the allylic moiety is the one controlling the stereochemical outcome and the stereoselectivity may also be affected by the conformational anomeric effect. This reaction has been applied for organic synthesis to form substituted tetrahydrofuran and γ-lactone derivatives.

Keywords:

  • allylic alcohol;
  • conformational anomeric effect;
  • polysubstituted tetrahydrofuran;
  • γ-lactone derivatives