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A Temporary Stereocentre Approach for the Stereodivergent Synthesis of Either Enantiomer of α-Methyloctanal

✍ Scribed by D. Gangani Niyadurupola; Iwan R. Davies; Richard Wisedale; Steven D. Bull

Publisher: John Wiley and Sons
Year: 2007
Tongue: English
Weight: 167 KB
Volume: 2007
Category: Article
ISSN: 1434-193X
DOI: 10.1002/ejoc.200700782

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✦ Synopsis

Abstract

The aldol reaction of a chiral N‐(acyl)oxazolidin‐2‐one with 2‐methyleneoctanal or (E)‐2‐methyloct‐2‐enal affords chiral aldol products whose alkene functionalities were hydrogenated using Brown's or Wilkinson's catalyst to afford syn‐ or anti‐selective products with excellent levels of diastereocontrol. Subsequent retro‐aldol cleavage of these syn‐ or anti‐adducts resulted in the formation of either (R)‐ or (S)‐enantiomer of α‐methyloctanal with no racemisation occurring, which could be derivatised in‐situ to afford chiral dithiane, alcohol or α,β‐unsaturated ester products in enantiopure form.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

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