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Asymmetric Synthesis of α‐Substituted Allyl Boranes and Their Application in the Synthesis of Iso‐agatharesinol
Author(s) -
Fang Guang Yu,
Aggarwal Varinder K.
Publication year - 2007
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.200603659
Subject(s) - boranes , stereospecificity , borane , chemistry , organic chemistry , boron , catalysis
Use your borane : A stereocontrolled synthesis of allyl boranes from chiral sulfur ylides and their subsequent reaction with aldehydes to give homoallylic alcohols is described. The allyl boranes also could undergo a stereospecific 1,3‐borotropic rearrangement to give another set of homoallylic alcohols (see scheme). The reaction has been applied to an efficient synthesis of iso‐agatharesinol.