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Stereoselective Allylic C–H Activation with Tertiary Alkylboranes: A New Method for Preparing Cycloalkyl Derivatives with Three Adjacent Stereocenters
Author(s) -
Lhermitte Frédéric,
Knochel Paul
Publication year - 1998
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/(sici)1521-3773(19981002)37:18<2459::aid-anie2459>3.0.co;2-o
Subject(s) - stereocenter , stereoselectivity , allylic rearrangement , diastereomer , hydroboration , chemistry , yield (engineering) , amination , stereochemistry , organic chemistry , enantioselective synthesis , catalysis , physics , thermodynamics
A regio‐ and stereoselective migration takes place under mild conditions for tertiary organoboranes obtained by hydroboration of tetrasubstituted cyclic alkenes. A subsequent amination proceeds with perfect control of the stereochemistry. The scheme shows an example of this for the reaction of bicyclo[4.3.0]non‐1(6)‐ene ( 1 ) to 2 via intermediates 3 and 4 . Compound 2 is formed as the single diastereomer in 69% yield.