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Catalytic Asymmetric Synthesis of Chiral Dihydrobenzofurans through a Formal [4+1] Annulation Reaction of Sulfur Ylides and In Situ Generated ortho ‐Quinone Methides
Author(s) -
Yang QingQing,
Xiao WenJing
Publication year - 2017
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201601186
Subject(s) - chemistry , annulation , catalysis , sulfur , enantioselective synthesis , enantiomer , quinone , in situ , formal synthesis , organic chemistry , combinatorial chemistry , medicinal chemistry
The first example of a catalytic asymmetric formal [4+1] annulation reaction between sulfur ylides and in situ generated ortho ‐quinone methides ( o ‐QMs) is reported in this work. A C 2‐symmetric chiral urea was identified to be the best H‐bonding catalyst, affording a wide range of chiral 2,3‐dihydrobenzofurans in high yields and moderate enantioselectivities [70–98 % yields, up to 89:11 e.r. (enantiomeric ratio)].