Synthesis 2002(14): 1973-1978
DOI: 10.1055/s-2002-34377
PAPER
© Georg Thieme Verlag Stuttgart · New York

Highly Diastereoselective Ketone Aldol Reactions of Butane-2,3-diacetal Desymmetrised­ Glycolic Acid

Darren J. Dixona, Antonio Guarnab, Steven V. Ley*a, Alessandra Polaraa, Félix Rodrígueza
a Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge CB2 1EW, UK
Fax: +44(1223)336442; e-Mail: svl1000@cam.ac.uk;
b Dipartimento di Chimica Organica ‘Ugo Schiff’, Università degli Studi di Firenze, Polo Scientifico, Via della Lastruccia, 13, 50019 Sesto Fiorentino, Italy
Further Information

Publication History

Received 13 June 2002
Publication Date:
26 September 2002 (online)

Abstract

Butane-2,3-diacetal (BDA) desymmetrised glycolic acid building block 1 undergoes highly diastereoselective lithium enolate ketone aldol reactions with a range of methyl and mono-substituted methyl ketones to yield, after acid-catalysed deprotection, enantiopure α,β-dihydroxy acid derivatives bearing a quaternary carbon atom at the β-hydroxy centre.