Direct asymmetric Zn-aldol reaction of methyl vinyl ketone and its synthetic applications.
A direct catalytic asymmetric aldol reaction of methyl vinyl ketone is described using our dinuclear zinc catalyst. The obtained aldol adduct functions as a bifunctional building block by utilization of the vinyl functionality. For example, convergent fragment coupling methods have been demonstrated via highly diastereoselective cycloaddition of nitrile oxide after reduction into 1,3-diol or via cross-metathesis reaction.
Trost
Barry M
BM
Department of Chemistry, Stanford University, Stanford, California 94305-5080, USA. bmtrost@Stanford.edu
Shin
Seunghoon
S
Sclafani
Joseph A
JA
D000438:Alcohols / Q000138:chemical synthesis*; D000447:Aldehydes / Q000737:chemistry*; D002074:Butanones / Q000737:chemistry*; D007659:Ketones / Q000138:chemical synthesis*; D015032:Zinc / Q000737:chemistry*
D000438:Alcohols; D000447:Aldehydes; D002074:Butanones; D007659:Ketones; C057920:3-buten-2-one; D015032:Zinc