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4‐Aminothioureaprolinal Dithioacetal as a Catalyst for Highly Enantioselective Michael Additions of Ketones and Aldehydes to Nitroolefins
Author(s) -
Chuan YongMing,
Yin LiYang,
Zhang YanMei,
Peng YunGui
Publication year - 2011
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201001211
Subject(s) - chemistry , michael reaction , enantioselective synthesis , catalysis , yield (engineering) , organic chemistry , adduct , solvent , materials science , metallurgy
4‐Aminothioureaprolinal dithioacetal 4a is a highly efficient catalyst for the asymmetric Michael addition of ketones and aldehydes to nitroolefins requiring only 3 mol‐% catalyst loading. The reactions proceeded smoothly and gave syn selective adducts with excellent yields (up to 98 % yield), diastereoselectivity (up to >99:1 dr ), and enantioselectivity (up to 99 % ee ) under solvent free conditions at room temperature. This extremely simple and practical procedure increases the attractiveness of this reaction.