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Synthesis of Binaphthyl Sulfonimides and Their Application in the Enantioselective Michael Addition of Ketones to Nitroalkenes
Author(s) -
Ban Shurong,
Du DaMing,
Liu Han,
Yang Wen
Publication year - 2010
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.201000818
Subject(s) - enantioselective synthesis , chemistry , michael reaction , optically active , organocatalysis , proline , organic chemistry , combinatorial chemistry , catalysis , amino acid , biochemistry
Novel types of L ‐proline‐based binaphthyl sulfonimides and sulfonamides were found to be efficient organocatalysts for the asymmetric Michael addition of ketones to nitroalkenes to provide optically active γ‐nitroketone derivatives of synthetic and biological importance. After the fine optimization of solvents, temperature, and additive, good to excellent enantioselectivities and diastereoselectivities (71–96 % ee , up to >99:1 dr ) can be achieved.