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

D G Niyadurupola, Iwan R Davies, R Wisedale, S D Bull

Research output: Contribution to journalArticle

11 Citations (Scopus)

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)-enanti-omer 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.
Original languageEnglish
Pages (from-to)5487-5491
Number of pages5
JournalEuropean Journal of Organic Chemistry
Volume2007
Issue number33
DOIs
Publication statusPublished - 2007

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