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2004
Carboxylic acid esters
Q 0530
TMSCl-Mediated Catalytic Carbocupration of Alkynoates: An Unprecedented
Remarkable Effect of Catalyst Loading on Highly Selective Stereochemical
46- 085 and
Induction via a TMS-Allenoate Intermediate. — Only catalytic amounts of a copper(I) salt (30—50 mol%) are necessary to obtain α,β-unsaturated carboxylic esters
from the title reaction of alkynoates (I) or (V) with Grignard reagents in good yields
and with high (E)-selectivities. For the reaction of alkynoate (I) with PhMgBr an
increasing E/Z ratio of the products is observed with increasing amounts of copper catalyst. Even the difference in the E/Z ratio between 20 and 30 mol% is unprecedented.
— (JENNINGS*, M. P.; SAWANT, K. B.; Eur. J. Org. Chem. 2004, 15, 3201-3204;
Dep. Chem., Univ. Ala., Tuscaloosa, AL 35487, USA; Eng.) — Klein
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