Enantioselective Construction of a 2,8-Dioxabicyclo[3.2.1]octane Ring System via [2,3]-Sigmatropic Rearrangement of Oxonium Ylide Using Chiral Dirhodium(II) Carboxylates

Shimada N; Nakamura S; Anada M; Shiro M; Hashimoto S

Chemistry Letters, Vol.38, No.5, 488-489, 2009

DOI10.1246/cl.2009.488 Export Citation

Enantioselective Construction of a 2,8-Dioxabicyclo[3.2.1]octane Ring System via [2,3]-Sigmatropic Rearrangement of Oxonium Ylide Using Chiral Dirhodium(II) Carboxylates

Shimada N, Nakamura S, Anada M, Shiro M, Hashimoto S

Dirhodium(II) tetrakis[N-tetrafluorophthaloyl-(S)-tert-leucinate], Rh-2(S-TFPTTL)(4), is an exceptionally efficient catalyst for enantioselective tandem cyclic oxonium ylide formation and [2.3]-sigmatropic rearrangement from alpha-diazo-beta-ketoester bearing cyclic allylic acetal functionality, providing the 2,8-dioxabicyclo[3.2.1]octane core structure of zaragozic acids in up to 93% ee.