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

Reference:

Niyadurupola, D. G., Davies, I. R., Wisedale, R. and Bull, S. D., 2007. A Temporary Stereocentre Approach for the Stereodivergent Synthesis of Either Enantiomer of α-Methyloctanal. European Journal of Organic Chemistry, 2007 (33), pp. 5487-5491.

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Official URL:

http://dx.doi.org/10.1002/ejoc.200700782

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.

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