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Iterative Asymmetric Allylic Substitutions: syn ‐ and anti ‐1,2‐Diols through Catalyst Control
Author(s) -
Park Jin Kyoon,
McQuade D. Tyler
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.201107874
Subject(s) - allylic rearrangement , catalysis , scheme (mathematics) , chemistry , group (periodic table) , combinatorial chemistry , copper , stereochemistry , medicinal chemistry , organic chemistry , mathematics , mathematical analysis
A copper‐catalyzed asymmetric allylic boronation (AAB) gives access to syn ‐ and anti ‐1,2‐diols. The method facilitates an iterative strategy for the preparation of polyols (see scheme), such as the fully differentiated L ‐ribo‐ tetrol and protected D ‐arabino‐ tetrol. P=protecting group