Synthesis of a new N-acetyl thiazolidinethione reagent and its application to a highly selective asymmetric acetate aldol reaction.
[reaction: see text] A new N-acetyl thiazolidinethione reagent, which undergoes highly diastereoselective aldol reactions upon enolization with dichlorophenylborane and (-)-sparteine and subsequent treatment with a variety of aldehydes, is described. This reagent is pseudoenantiomeric to an L-tert-leucine-derived reagent recently described by us and is useful because it avoids the prohibitively costly D-tert-leucine.
Zhang
Yingchao
Y
Department of Chemistry and Biochemistry, University of Colorado, Boulder, Colorado 80309-0215, USA.
Sammakia
Tarek
T
D000447:Aldehydes / Q000737:chemistry*; D002625:Chemistry, Organic / Q000379:methods; D007202:Indicators and Reagents; D007930:Leucine / Q000031:analogs & derivatives* / Q000737:chemistry*; D015394:Molecular Structure; D013034:Sparteine / Q000737:chemistry; D013237:Stereoisomerism; D013844:Thiazoles / Q000138:chemical synthesis*
D000447:Aldehydes; D007202:Indicators and Reagents; D013844:Thiazoles; D013034:Sparteine; D007930:Leucine