(Dichloromethyl)dimethylsilyl Group as a Hydroxymethylidene Diradical  Equivalent: Radical Annulation of Dienols and Its Application to the Stereoselective  Synthesis of of cis- and trans-Hydrindan Ring Systems

K. Tamao; K. Nagata; Y. Ito; K. Maeda; M. Shiro

doi:10.1055/s-1994-22818

Synlett 1994; 1994(4): 257-259
DOI: 10.1055/s-1994-22818

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(Dichloromethyl)dimethylsilyl Group as a Hydroxymethylidene Diradical Equivalent: Radical Annulation of Dienols and Its Application to the Stereoselective Synthesis of of cis- and trans-Hydrindan Ring Systems

K. Tamao^* , K. Nagata, Y. Ito, K. Maeda, M. Shiro

^*Institute for Chemical Research, Kyoto University, Uji, Kyoto 611, Japan

Abstract

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(Dichloromethyl)dimethylchlorosilane has been used as the hydroxymethylidene diradical as well as the formyl radical equivalents for allyl alcohol derivatives via hydrostannane or allylstannane mediated radical cyclization followed by oxidative cleavage of the carbon-silicon bonds. The new radical annulation method has been applied to the stereo-controlled construction of cis- and trans-hydrindan skeletons.

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