Enantioselective Formal C(sp2)-H Vinylation.
An enantioselective formal C(sp2)-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.
Department of Organic Chemistry, Indian Institute of Science, Bangalore, 560 012, India.
Madhu Sudan
http://orcid.org/0000-0003-0364-4947
MS
Manna
Department of Organic Chemistry, Indian Institute of Science, Bangalore, 560 012, India.
Rahul
http://orcid.org/0000-0003-3700-6580
R
Sarkar
Department of Organic Chemistry, Indian Institute of Science, Bangalore, 560 012, India. sm@orgchem.iisc.ernet.in.
Santanu
http://orcid.org/0000-0001-9651-6228
S
Mukherjee
C−H functionalization; decarboxylation; desymmetrization; lactones; vinylation