Stereoselective conjugate addition of ketones to alkylidene malonates using thiourea-sulfonamide organocatalyst

Masahiro Kawada; Kosuke Nakashima; Shin-Ichi Hirashima; Toru Sakagami; Yuji Koseki; Tsuyoshi Miura

doi:10.1002/chir.23015

Stereoselective conjugate addition of ketones to alkylidene malonates using thiourea-sulfonamide organocatalyst

Chirality. 2018 Nov;30(11):1215-1224. doi: 10.1002/chir.23015. Epub 2018 Sep 13.

Authors

Masahiro Kawada¹, Kosuke Nakashima¹, Shin-Ichi Hirashima¹, Toru Sakagami¹, Yuji Koseki¹, Tsuyoshi Miura¹

Affiliation

¹ School of Pharmacy, Tokyo University of Pharmacy and Life Sciences, Hachioji, Japan.

PMID: 30211959
DOI: 10.1002/chir.23015

Abstract

In this study, stereoselective conjugate addition of ketones to alkylidene malonates using organocatalyst has been developed. The reaction in the presence of 20 mol% of a novel thiourea-sulfonamide organocatalyst afforded conjugate adducts in moderate to high yields (up to 81%) under mild reaction conditions. Excellent diastereoselectivity (up to 98:2 dr) and enantioselectivity (up to 88% ee) were achieved.

Keywords: alkylidene malonate; asymmetric conjugate addition; organocatalysis; organocatalyst; thiourea-sulfonamideIntroduction.

Publication types

Research Support, Non-U.S. Gov't

Grants and funding

16K08178/JSPS KAKENHI/International