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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.