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Synthesis 2011(13): 2062-2065  
DOI: 10.1055/s-0030-1259989
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© Georg Thieme Verlag Stuttgart ˙ New York

Shortened Synthesis of a Silicon-Stereogenic Cyclic Silane

C. David F. Königs, Martin Oestreich*
Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstr. 40, 48149 Münster, Germany
Fax: +49(251)8336501; e-Mail: martin.oestreich@uni-muenster.de;
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Publication History

Received 2 March 2011
Publication Date:
05 April 2011 (online)

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Abstract

The previous racemic synthesis of a six-membered ring silane from tert-butyltrichlorosilane required six steps (22% overall yield). A considerably shortened reaction sequence now allows for its preparation from rarely used tert-butylsilane in only two steps (42% overall yield). The new access also offers more facile purification of the intermediate(s) and the target compound.

Key words

cyclization - Grignard reaction - hydrosilylation - nucleophilic substitution - silicon

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17

For RSiH3 with R = alkyl but not aryl, the effect of LiCl is less pronounced (cf. Equation 8 in ref. 12).