Premium
A One‐Pot Cross‐Metathesis/Allylboration Reaction: A Three‐Component Coupling for the Synthesis of Functionalized Homoallylic Alcohols
Author(s) -
Goldberg Steven D.,
Grubbs Robert H.
Publication year - 2002
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 - 10.1002/1521-3773(20020301)41:5<807::aid-anie807>3.0.co;2-v
Subject(s) - allylic rearrangement , reagent , steric effects , chemistry , olefin metathesis , metathesis , olefin fiber , halide , organic chemistry , combinatorial chemistry , catalysis , polymer , polymerization
Reactive reagents can be prepared by means of olefin cross‐metathesis. A wide variety of functionalized allyl boronates were synthesized and were found to react cleanly with aldehydes to afford homoallylic alcohols, without prior purification (see scheme). Olefins that bear allylic ethers, halides, protected aldehydes, and sterically encumbering groups are viable substrates for this reaction.