Mc. Guerreiro et U. Schuchardt, SITE AND STEREOSELECTIVITY OF THE CYCLOPROPANATION OF UNSYMMETRICALLYSUBSTITUTED 1,3-DIENES BY THE SIMMONS-SMITH REACTION, Synthetic communications, 26(9), 1996, pp. 1793-1800
In the Simmons-Smith reaction, 1,3-dienes are preferentially cycloprop
anated at the more electron-rich double bond to afford the trans-vinyl
cyclopropane; an allylic hydroxyl group increases the reactivity and d
irects the cyclopropanation to the adjacent double bond.