Indene-based thiazolidinethione chiral auxiliary for propionate and acetate aldol additions

  • Org Lett. 2008 Feb 21;10(4):617-20. doi: 10.1021/ol702980p.
Antonio Osorio-Lozada  1 ,  Horacio F Olivo
Affiliations
  • 1. Division of Medicinal and Natural Products Chemistry, The University of Iowa, Iowa City, Iowa 52242, USA.
PMID: 18205374 DOI: 10.1021/ol702980p
Abstract

An indene-based thiazolidinethione chiral auxiliary was prepared in two steps from trans-1-amino-2-indanol. Chlorotitanium enolates of this chiral auxiliary delivered excellent diastereoselectivities in propionate and acetate aldol additions. The chiral auxiliary was easily removed to deliver several valuable functionalities.

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