STEREOSELECTIVITY IN THE MICHAEL REACTION. II. STEREOCHEMISTRY OF A HEAVILY SUBSTITUTED ALKENE

I CROSSLAND, K BOCK…

Index: Crossland, Ingolf; Bock, Klaus; Norrestam, Rolf Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry, 1985 , vol. 39, # 1 p. 7 - 14

Full Text: HTML

Citation Number: 4

Abstract

The trimethysilylated primary Michael adduct of tricarbomethoxymethane and 2-bromo-3- oxo-3-phenylpropeue-1 is shown by 'H NMR experiments and X-ray diffraction studies to possess the structure Z-2. Attempts to prepare the E isomer via the hydrolysis product of Z-2 resulted in, inter alia, an intramolecular alkylation under decarbomethoxylation to give the cyclopropane ester 4.