The Journal of Organic Chemistry

Cyclopentene and cyclohexene annulation via copper-catalyzed conjugate addition of acetal-containing Grignard reagents

SA Bal, A Marfat, P Helquist

Index: Bal, Swati A.; Marfat, Anthony; Helquist, Paul Journal of Organic Chemistry, 1982 , vol. 47, # 26 p. 5045 - 5050

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Citation Number: 110

Abstract

The Grignard reagents 2 derived from 2-(2bromoethyl)-and 2-(3-chloropropyl)-l, 3-dioxolane undergo conjugate addition to a number of a, B-unsaturated ketones in the presence of a catalytic amount of a cuprous salt. The resulting keto acetals, upon treatment with hydrochloric acid, undergo sequential hydrolysis, intramolecular aldol condensation, and dehydration to give cyclopentene and cyclohexene annulation products. The entire series ...