Enantiospecific and regioselective rhodium-catalyzed allylic alkylation: diastereoselective approach to quaternary carbon stereogenic centers.
The enantiospecific and regioselective rhodium-catalyzed allylic alkylation of a series of chiral nonracemic allylic carbonates, followed by ozonolysis and reductive lactonization, provides a convenient route to optically active gamma-lactones. Sequential alkylation and reductive alkylation furnished the alpha-quaternary-beta-ternary substituted gamma-lactone derivative as a >/=10:1 mixture of diastereoisomers.
Evans
P A
PA
Brown Laboratory, Department of Chemistry and Biochemistry, University of Delaware, Newark, Delaware 19716, USA. iyoda@c.metro-u.ac.jp
Kennedy
L J
LJ
D000478:Alkylation; D002244:Carbon / Q000737:chemistry / Q000378:metabolism; D002254:Carbonates / Q000737:chemistry* / Q000378:metabolism*; D002384:Catalysis; D007783:Lactones / Q000138:chemical synthesis* / Q000378:metabolism; D012238:Rhodium / Q000737:chemistry* / Q000378:metabolism; D013237:Stereoisomerism; D013379:Substrate Specificity
D002254:Carbonates; D007783:Lactones; D002244:Carbon; D012238:Rhodium