First Atropo‐Enantioselective Ring Opening of Achiral Biaryls Containing Lactone Bridges with Chiral Hydride‐Transfer Reagents Derived from Borane | Zendy

Bringmann Gerhard | Zendy; Hartung Thomas | Zendy

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First Atropo‐Enantioselective Ring Opening of Achiral Biaryls Containing Lactone Bridges with Chiral Hydride‐Transfer Reagents Derived from Borane

Author(s) -

Bringmann Gerhard,

Hartung Thomas

Publication year - 1992

Publication title -

angewandte chemie international edition in english

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 0570-0833

DOI - 10.1002/anie.199207611

Subject(s) - enantioselective synthesis , borane , nucleophile , chemistry , ring (chemistry) , lactone , reagent , alcohol , recrystallization (geology) , hydride , stereochemistry , combinatorial chemistry , organic chemistry , catalysis , hydrogen , paleontology , biology

An impressive example of the directed “twisting” of bridged, configuratively labile biaryls with chiral H ‐nucleophiles is seen in the atropo‐enantioselective, ring‐opening reduction of lactone 1 to alcohol 2 with borane THF in the presence of the chiral oxazaborolidine 3 . After one recrystallization 2 is enantiomerically pure.

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