Silylative carbocyclization of allenyl-carbonyl units with Et3SiH catalyzed by rhodium: cis-stereoselective synthesis of homoallylic cycloalkanols

Org Lett. 2003 Aug 7;5(16):2813-6. doi: 10.1021/ol034787k.

Abstract

[reaction: see text] A new procedure for the synthesis of cis-2-triethylsilylvinyl-cyclopentanols and -cyclohexanols from allenyl-aldehydes and -ketones with Et(3)SiH through rhodium-catalyzed silylative carbocyclization is described. The use of Rh(acac)(CO)(2) (1 mol %) to promote the reaction results in a mild and convenient protocol for the three-component assembly.