Catalytic Asymmetric Synthesis of Chiral Dihydrobenzofurans through a Formal [4+1] Annulation Reaction of Sulfur Ylides and In Situ Generated  ortho ‐Quinone Methides | Zendy

Yang QingQing | Zendy; Xiao WenJing | Zendy

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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)].

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