L-selectride-mediated highly diastereoselective asymmetric reductive aldol reaction: access to an important subunit for bioactive molecules.
L-selectride reduction of a chiral or achiral enone followed by reaction of the resulting enolate with optically active alpha-alkoxy aldehydes proceeded with excellent diastereoselectivity. The resulting alpha,alpha-dimethyl-beta-hydroxy ketones are inherent to a variety of biologically active natural products.
Ghosh
Arun K
AK
Department of Chemistry, Purdue University, West Lafayette, Indiana 47907, USA. akghosh@purdue.edu
Kass
Jorden
J
Anderson
David D
DD
Xu
Xiaoming
X
Marian
Christine
C
D000447:Aldehydes / Q000737:chemistry*; D001688:Biological Products / Q000737:chemistry; D001880:Boranes / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013237:Stereoisomerism
D000447:Aldehydes; D001688:Biological Products; D001880:Boranes; C533353:selectride; C116609:3-hydroxybutanal