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Boron‐Catalyzed Regioselective Deoxygenation of Terminal 1,2‐Diols to 2‐Alkanols Enabled by the Strategic Formation of a Cyclic Siloxane Intermediate
Author(s) -
Drosos Nikolaos,
Morandi Bill
Publication year - 2015
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.201503172
Subject(s) - deoxygenation , regioselectivity , catalysis , siloxane , boron , chemistry , combinatorial chemistry , enantiomer , organic chemistry , polymer
Abstract The selective deoxygenation of polyols is a frontier in our ability to harness the stereochemical and structural complexity of natural and synthetic feedstocks. Herein, we describe a highly active and selective boron‐based catalytic system for the selective deoxygenation of terminal 1,2‐diols at the primary position, a process that is enabled by the transient formation of a cyclic siloxane. The method provides an ideal complement to well‐known catalytic asymmetric reactions to prepare synthetically challenging chiral 2‐alkanols in nearly perfect enantiomeric excess, as illustrated in a short synthesis of the anti‐inflammatory drug ( R )‐lisofylline.