Issue 47, 2016

Synthesis of α-methylene-δ-oxo-γ-amino esters via Rh(ii)-catalyzed coupling of 1-sulfonyl-1,2,3-triazoles with Morita–Baylis–Hillman adducts

Abstract

A rhodium(II)-catalyzed coupling of 1-sulfonyl-1,2,3-triazoles, prepared from 1-alkynes and sulfonyl azides, with Morita–Baylis–Hillman (MBH) adducts afforded highly functionalized α-methylene-δ-oxo-γ-amino esters in excellent yields with broad functional group tolerance. This transformation can also be successfully accomplished as a multicomponent all-in-one-pot reaction of 1-alkynes, sulfonyl azides and MBH adducts in the presence of Cu(I) and Rh(II) catalysts.

Graphical abstract: Synthesis of α-methylene-δ-oxo-γ-amino esters via Rh(ii)-catalyzed coupling of 1-sulfonyl-1,2,3-triazoles with Morita–Baylis–Hillman adducts

Supplementary files

Article information

Article type
Paper
Submitted
22 Sep 2016
Accepted
09 Nov 2016
First published
16 Nov 2016

Org. Biomol. Chem., 2016,14, 11238-11243

Synthesis of α-methylene-δ-oxo-γ-amino esters via Rh(II)-catalyzed coupling of 1-sulfonyl-1,2,3-triazoles with Morita–Baylis–Hillman adducts

H. J. Jeon, M. S. Kwak, D. J. Jung, J. Bouffard and S. Lee, Org. Biomol. Chem., 2016, 14, 11238 DOI: 10.1039/C6OB02086K

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