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Asymmetric Synthesis of Dihydrocoumarins Containing Contiguous Quaternary and Tertiary Stereogenic Centers Catalyzed by a Cinchona ‐Alkaloid‐Based Bifunctional Thiourea Derivative
Author(s) -
Zhang ShaoYun,
Lv Ming,
Yin ShaoJie,
Li NaiKai,
Zhang JunQi,
Wang XingWang
Publication year - 2016
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201500666
Subject(s) - stereocenter , bifunctional , chemistry , cinchona , thiourea , domino , enantioselective synthesis , organocatalysis , organic chemistry , michael reaction , catalysis
A series of enantiomerically enriched 3,4‐dihydrocoumarins containing contiguous quaternary and tertiary stereogenic centers has been efficiently constructed via domino asymmetric Michael addition/transesterification reactions of azlactones with o ‐hydroxychalcones using a quinine‐derived thiourea as bifunctional organocatalyst. Under mild reaction conditions, the optically active 3,4‐dihydrocoumarins were generally obtained in 63–96% yields with >20:1 dr and 81–96% ee .