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Reaction of (trimethylstannyl) copper reagents with α, β-acetylenic esters

✍ Scribed by Edward Piers; J.Michael Chong; Howard E. Morton

Publisher
Elsevier Science
Year
1981
Tongue
French
Weight
303 KB
Volume
22
Category
Article
ISSN
0040-4039

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✦ Synopsis

The stereochemical course of the conjugate addition of various (trimethylstannyl)cuprate (or copper) reagents to cr,B-acetylenic esters is dependent on the constitution of the reagent and on the structure of the substrate.

Recently, it was reported 1 that the conjugate addition of lithium (phenylthio)(trimethylstannyl)cuprate Q2 to a,B-acetylenic esters (e.g. ethyl 2-butynoate, lJ3 can be controlled experimentally so as to produce, stereoselectively, either of the geometrically isomeric products 3 (the product of kinetic control) or f? (the product of thermodynamic control). Thus, reaction of &, with 2_ (THF, -78'C) in the presence of a small amount of methanol or ethanol produced the E isomer 2 (>99% isomerically pure). Apparently, under these reaction conditions, the "kinetic" intermediate (cf. 7)4 protonates CH, -ti C0&' CH, H more rapidly than it isomer&es. Cl%-C-C-C02Et + [Me,SnCuS&H,] LIt( -+ -

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