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Vinyl‐, Propargyl‐, and Allenylsilicon Reagents in Asymmetric Synthesis: A Relatively Untapped Resource of Environmentally Benign Reagents
Author(s) -
CurtisLong Marcus J.,
Aye Yimon
Publication year - 2009
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200900337
Subject(s) - carbanion , propargyl , reagent , reactivity (psychology) , stereoselectivity , chemistry , organic chemistry , combinatorial chemistry , nanotechnology , materials science , catalysis , medicine , alternative medicine , pathology
Green carbanion surrogates : Organotrialkylsilanes occupy a niche in the array of ‘green’ carbon nucleophiles open to chemists that few other reagents can fill. Despite being known for over 30 years, it is only recently that their true worth in stereoselective carbonyl addition and related processes has started to emerge, primarily due to their low reactivity. It is our hope that this minireview will make the true worth of these reagents more widely known, setting the stage for expanded usage of these versatile yet benign reagents in organic synthesis.An up‐to‐date in‐depth review of the current virtues and limitations in the realm of carbonyl addition reactions with allenyl‐, propargyl‐, and vinylsilicon reagents, encompassing numerous practical as well as pedagogical principles is presented. Comparisons of chemo‐, regio‐, and stereoselectivity and reactivity are drawn. Synthetic applications and challenges associated with each class of organosilane are discussed threading together the prospects of these green carbanion surrogates.