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Asymmetric Michael Addition of N ‐Boc‐Protected Oxindoles to Nitroalkenes Catalyzed by a Chiral Secondary Amine
Author(s) -
Wang Chuan,
Yang Xuena,
Enders Dieter
Publication year - 2012
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.201200079
Subject(s) - amine gas treating , michael reaction , chemistry , base (topology) , catalysis , organocatalysis , organic chemistry , combinatorial chemistry , computer science , enantioselective synthesis , mathematics , mathematical analysis
New mission for prolinol ethers : A secondary‐amine‐catalyzed Michael addition of N ‐Boc‐protected oxindoles to nitroalkenes through a Brønsted base activation mode has been developed, furnishing the products in excellent yields (88–98 %), diastereoselectivities (d.r.=98:2–>99:1) and high to excellent enantioselectivities (82–>99 % ee ; see scheme).