TY - JOUR
T1 - Phosphoramidites are efficient, green organocatalysts for the Michael reaction. Mechanistic insights into the phosphorus-catalyzed Michael reaction of alkynones and implications for asymmetric catalysis
AU - Grossman, Robert B.
AU - Comesse, Sébastien
AU - Rasne, Ravindra M.
AU - Hattori, Kazuyuki
AU - Delong, Matthew N.
N1 - Copyright:
Copyright 2011 Elsevier B.V., All rights reserved.
PY - 2003/2/7
Y1 - 2003/2/7
N2 - Hexamethylphosphorous triamide (HMPT) and other phosphoramidites and phosphites have been found to be efficient catalysts for the Michael reaction of alkenones and alkynones with malonates, α-cyano esters, β-keto esters, and nitro compounds. The relatively nontoxic, easily hydrolyzed HMPT catalyzes the Michael reaction within seconds at room temperature in the absence of a solvent, and the reaction is worked up simply by removing the catalyst in vacuo. The Michael reactions of alkynones, unlike those of alkenones, are shown to be irreversible. The implications for asymmetric catalysis are discussed.
AB - Hexamethylphosphorous triamide (HMPT) and other phosphoramidites and phosphites have been found to be efficient catalysts for the Michael reaction of alkenones and alkynones with malonates, α-cyano esters, β-keto esters, and nitro compounds. The relatively nontoxic, easily hydrolyzed HMPT catalyzes the Michael reaction within seconds at room temperature in the absence of a solvent, and the reaction is worked up simply by removing the catalyst in vacuo. The Michael reactions of alkynones, unlike those of alkenones, are shown to be irreversible. The implications for asymmetric catalysis are discussed.
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U2 - 10.1021/jo026425g
DO - 10.1021/jo026425g
M3 - Article
C2 - 12558409
AN - SCOPUS:0037423171
SN - 0022-3263
VL - 68
SP - 871
EP - 874
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 3
ER -