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Julia Olefination

(Julia-Kocienski Olefination or Julia-Lythgoe Olefination)

Published Online: 15 SEP 2010

DOI: 10.1002/9780470638859.conrr351

Comprehensive Organic Name Reactions and Reagents

Comprehensive Organic Name Reactions and Reagents

How to Cite

2010. Julia Olefination. Comprehensive Organic Name Reactions and Reagents. 351:1576–1582.

Publication History

  1. Published Online: 15 SEP 2010

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Abstract

The multistep preparation of trans-olefins involving the addition of phenylsulfonyl carbanion to aldehydes or ketones to form β-hydroxysulfones, followed by the esterification of hydroxyl group and reductive elimination of β-sulfonyl esters with sodium amalgam is generally referred to as the Julia olefination. Because of its intrinsic weaknesses, Julia olefination protocol has been extensively modified and extended. These modifications employ the one-step reaction between heterocyclic sulfonyl carbanion and aldehyde (or ketone) to give either cis- or trans-olefins or replace the reduction from the sodium amalgam by samarium iodide (SmI2). Therefore, the modified olefination methods are referred to as the Kocienski olefination. Several heterocyclic sulfones in this olefination reaction have been suggested and it has been reported that the application of heterocyclic sulfones in this olefination provides extra advantages. This reaction has wide application in the preparation of olefins, particularly in the convergent synthesis of complex natural products.

Keywords:

  • Kocienski olefination;
  • β-hydroxysulfones;
  • heterocyclic sulfones;
  • allyl sulfones