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Organosuperbase‐catalyzed Direct‐type Michael Addition Reactions of Sulfonylimidates as Ester Surrogates
Author(s) -
Masuda Koichiro,
Nakano Junya,
Yamashita Yasuhiro,
Kobayashi Shū
Publication year - 2013
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201300014
Subject(s) - chemistry , catalysis , steric effects , aryl , michael reaction , organic chemistry , alcohol , combinatorial chemistry , alkyl
A super catalyst! Highly diastereoselective Michael addition reactions of sulfonylimidates with α,β‐unsaturated thioesters have been developed by using organosuperbases as highly efficient catalysts. The diastereoselectivity of the reactions was successfully controlled by the steric bulkiness of the aryl group on the sulfonylimidates. The obtained products were successfully converted into an amino alcohol and an ester. PAP=proazaphosphatrane.