Stereoselective conjugate addition of ketones to alkylidene malonates using thiourea‐sulfonamide organocatalyst | Zendy

Kawada Masahiro | Zendy; Nakashima Kosuke | Zendy; Hirashima Shinichi | Zendy; Sakagami Toru | Zendy; Koseki Yuji | Zendy; Miura Tsuyoshi | Zendy

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

Author(s) -

Kawada Masahiro,

Nakashima Kosuke,

Hirashima Shinichi,

Sakagami Toru,

Koseki Yuji,

Miura Tsuyoshi

Publication year - 2018

Publication title -

chirality

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.43

H-Index - 77

eISSN - 1520-636X

pISSN - 0899-0042

DOI - 10.1002/chir.23015

Subject(s) - chemistry , sulfonamide , conjugate , thiourea , stereoselectivity , adduct , organocatalysis , organic chemistry , addition reaction , enantioselective synthesis , catalysis , combinatorial chemistry , mathematical analysis , mathematics

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.

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