Organic Chemistry Portal

Abstracts

Search:

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


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.

see article for more examples



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