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Novel Prolinamide–Camphor‐Containing Organocatalysts for Direct Asymmetric Michael Addition of Unmodified Aldehydes to Nitroalkenes
Author(s) -
Reddy Raju Jannapu,
Kuan HsuanHao,
Chou TsaiYung,
Chen Kwunmin
Publication year - 2009
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200901254
Subject(s) - michael reaction , camphor , enantioselective synthesis , organocatalysis , chemistry , addition reaction , computer science , organic chemistry , catalysis
The asymmetric challenge! New camphor‐based prolinamides were designed, synthesized, and proven to be a highly efficient organocatalysts for asymmetric Michael reactions. Treatment of unmodified aldehydes with nitroalkenes in the presence of 5–10 mol % organocatalysts provided the desired Michael products in high chemical yields (up to 94 %) and high to excellent levels of diastereo‐ and enantioselectivities (up to 99:1 d.r. and>99 % ee ).