Chemical and Pharmaceutical Bulletin p. 398 - 402 (1995)
Update date:2022-08-04
Topics:
Itaya
Shimizu
Among N-protected and unprotected vinylglycines tested, N-(benzyloxycarbonyl)vinylglycine (1c) provided the highest yield of the coupling product 3c in the reaction with 1-iodo-4-methoxybenzene (2) in N,N-dimethylformamide in the presence of palladium acetate, sodium bicarbonate, and tetrabutylammonium chloride, whereas none of the desired product was obtained in the reaction with 4-methoxyphenyl trifluoromethanesulfonate (7). The stereo-selectivity of the reaction was reversed by employing triethylamine instead of sodium bicarbonate to furnish (Z)-3c predominantly. In the presence of sodium bicarbonate, replacement of the solvent by water improved not only the chemical yield and stereo-selectivity but also the optical purity: geometiically pure (E)-3c of 96% ee was formed in a good yield.
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