Highly selective mild stepwise allylation of N-methoxybenzamides with allenes

Rong Zeng; Chunling Fu; Shengming Ma

doi:10.1021/ja303790s

Highly selective mild stepwise allylation of N-methoxybenzamides with allenes

J Am Chem Soc. 2012 Jun 13;134(23):9597-600. doi: 10.1021/ja303790s. Epub 2012 Jun 4.

Authors

Rong Zeng¹, Chunling Fu, Shengming Ma

Affiliation

¹ Laboratory of Molecular Recognition and Synthesis, Department of Chemistry, Zhejiang University, Hangzhou 310027, Zhejiang, P.R. China.

PMID: 22640007
DOI: 10.1021/ja303790s

Abstract

An efficient Rh(III)-catalyzed stepwise ortho allylation of N-methoxybenzamides 1 with polysubstituted allenes is reported. This C-H functionalization involving allenes is conducted under very mild conditions (-20 °C or room temperature) and compatible with ambient air and moisture, and it can be applied to terminal or internal allenes with different synthetically attractive functional groups. Highly efficient axial chirality transfer has been realized, yielding optically active lactones.