Highly selective asymmetric acetate aldol reactions of an N-acetyl thiazolidinethione reagent.
[reaction: see text] A highly diastereoselective acetate aldol reaction that uses a tert-leucine-derived thiazolidinethione auxiliary and dichlorophenylborane has been developed. The reaction proceeds in excellent yields and with high diastereoselectivities (drs range from 9.5:1 to >100:1).
Zhang
Yingchao
Y
Department of Chemistry and Biochemistry, University of Colorado, Boulder, Colorado 80309-0215, USA.
Phillips
Andrew J
AJ
Sammakia
Tarek
T
D000447:Aldehydes / Q000737:chemistry*; D001896:Boron Compounds / Q000737:chemistry; D002625:Chemistry, Organic / Q000379:methods; D007202:Indicators and Reagents; D007930:Leucine / Q000031:analogs & derivatives; D015394:Molecular Structure; D013237:Stereoisomerism; D013844:Thiazoles / Q000737:chemistry*; D014633:Valine / Q000031:analogs & derivatives* / Q000737:chemistry*
D000447:Aldehydes; D001896:Boron Compounds; D007202:Indicators and Reagents; D013844:Thiazoles; C089871:2-amino-3,3-dimethylbutanoic acid; D007930:Leucine; D014633:Valine