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Enantioselective C−C Bond Formation by Rhodium-Catalyzed Tandem Ylide Formation/[2,3]-Sigmatropic Rearrangement between Donor/Acceptor Carbenoids and Allylic Alcohols
- Source :
- Journal of the American Chemical Society. 132:396-401
- Publication Year :
- 2009
- Publisher :
- American Chemical Society (ACS), 2009.
-
Abstract
- The rhodium-catalyzed reaction of racemic allyl alcohols with methyl phenyldiazoacetate or methyl styryldiazoacetate results in a two-step process, an initial oxonium ylide formation followed by a [2,3]-sigmatropic rearrangement. This process competes favorably with the more conventional O-H insertion chemistry as long as donor/acceptor carbenoids and highly substituted allyl alcohols are used as substrates. When the reactions are catalyzed by Rh(2)(S-DOSP)(4), tertiary alpha-hydroxycarboxylate derivatives with two adjacent quaternary centers are produced with high enantioselectivity (85-98% ee).
Details
- ISSN :
- 15205126 and 00027863
- Volume :
- 132
- Database :
- OpenAIRE
- Journal :
- Journal of the American Chemical Society
- Accession number :
- edsair.doi.dedup.....fc741d5ce0d4b3d68302d623cb75a0a7