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[3,3] Sigmatropic Rearrangement of Boron‐Containing Allyl Alcohols: Synthesis of Allyl Addition Reagents
Author(s) -
Pietruszka Jörg,
Schöne Niklas
Publication year - 2003
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.200352210
Subject(s) - diastereomer , stereocenter , sigmatropic reaction , chemistry , reagent , enantiomer , boron , organic chemistry , enantioselective synthesis , catalysis
Enantiomerically pure reagents for allyl additions were prepared by [3,3] sigmatropic rearrangements (see scheme) followed by a separation of the diastereoisomers. The highly stable allylboronic esters with a stereogenic center α to a boron atom were used to synthesize Z ‐configured homoallylic alcohols with an enantiomeric excess >94 %.
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