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Enantioselective Formal C(sp 2 )−H Vinylation
Author(s) -
Manna Madhu Sudan,
Sarkar Rahul,
Mukherjee Santanu
Publication year - 2016
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.201602253
Subject(s) - enantioselective synthesis , desymmetrization , cyclopentene , stereocenter , decarboxylation , chemistry , stereochemistry , catalysis , organic chemistry
An enantioselective formal C(sp 2 )−H vinylation of prochiral 2,2‐disubstituted cyclopentene‐1,3‐dione is presented. This vinylative desymmetrization is realized by using a two‐step procedure that consists of a catalytic enantioselective vinylogous Michael addition of deconjugated butenolides to cyclopentene‐1,3‐dione and a base‐mediated decarboxylation. The overall process utilizes deconjugated butenolides as the source of the highly substituted vinyl unit. Five‐membered carbocycles containing a remote all‐carbon quaternary stereogenic center are obtained in good yields and with good to high enantioselectivities.