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Stereoselective Olefin Isomerization Leading to Asymmetric Quaternary Carbon Construction

Kan Wang, Christopher J. Bungard and Scott G. Nelson*

*Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, Email: sgnelsonpitt.edu

K. Wang, C. J. Bungard, S. G. Nelson, Org. Lett., 2007, 9, 2325-2328.

DOI: 10.1021/ol0706511 (free Supporting Information)


Abstract

Chemo- and stereoselective Ir(I)-catalyzed isomerization of 1,1-disubstituted and trisubstituted allylic ethers and in situ [3,3] sigmatropic rearrangement of the resulting allyl vinyl ethers provide for the highly stereoselective construction of quaternary carbon stereocenters.

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Asymmetric Claisen Rearrangements Enabled by Catalytic Asymmetric Di(allyl) Ether Synthesis

S. G. Nelson, K. Wang, J. Am. Chem. Soc., 2006, 128, 4232-4233.


Key Words

Claisen Rearrangement, Aldehydes


ID: J54-Y2007-1840