Highly stereoselective C-C bond formation by rhodium-catalyzed tandem ylide formation/[2,3]-sigmatropic rearrangement between donor/acceptor carbenoids and chiral allylic alcohols.
The tandem ylide formation/[2,3]-sigmatropic rearrangement between donor/acceptor rhodium carbenoids and chiral allyl alcohols is a convergent C-C bond forming process, which generates two vicinal stereogenic centers. Any of the four possible stereoisomers can be selectively synthesized by appropriate combination of the chiral catalyst Rh(2)(DOSP)(4) and the chiral alcohol.
Department of Chemistry, Emory University, 1515 Dickey Drive, Atlanta, Georgia 30322, USA.
Zhanjie
Z
Li
Brendan T
BT
Parr
Huw M L
HM
Davies
D000498:Allyl Compounds / Q000737:chemistry*; D001391:Azo Compounds / Q000737:chemistry; D002384:Catalysis; D009942:Organometallic Compounds / Q000737:chemistry; D011392:Proline / Q000031:analogs & derivatives / Q000737:chemistry; D020005:Propanols / Q000737:chemistry*; D012238:Rhodium / Q000737:chemistry; D013237:Stereoisomerism
D000498:Allyl Compounds; D001391:Azo Compounds; D009942:Organometallic Compounds; D020005:Propanols; C407352:dirhodium tetrakis(S-(N-dodecylbenzenesulfonyl)prolinate); C006463:allyl alcohol; D011392:Proline; D012238:Rhodium