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Rhodium(I)‐Catalyzed Domino Asymmetric Ring Opening/Enantioselective Isomerization of Oxabicyclic Alkenes with Water
Author(s) -
Tsui Gavin C.,
Lautens Mark
Publication year - 2012
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201200390
Subject(s) - enantioselective synthesis , isomerization , domino , ring (chemistry) , catalysis , chemistry , rhodium , stereochemistry , enantiomer , organic chemistry
Water‐induced asymmetric ring opening : Enantio‐enriched 2‐hydroxy‐1‐tetralones are formed from oxabicyclic alkenes through a novel Rh I ‐catalyzed domino reaction. The proposed mechanism involves water‐induced asymmetric ring opening to generate chiral trans ‐1,2‐diol intermediates and subsequent enantioselective isomerization (see scheme).