Highly Diastereoselective Hydrostannylation of Allyl and Homoallyl Alcohols with Dibutyl(trifluoromethanesulfoxy)stannane
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- 作者：Katsukiyo Miura ; Di Wang ; and Akira Hosomi
- 刊名：Journal of the American Chemical Society
- 出版年：2005
- 出版时间：July 6, 2005
- 年：2005
- 卷：127
- 期：26
- 页码：9366 - 9367
- 全文大小：50K
- 年卷期：v.127,no.26(July 6, 2005)
- ISSN：1520-5126
文摘
Dibutyl(trifluoromethanesulfoxy)stannane (Bu2Sn(OTf)H, 1a) was found to be very valuable for highly diastereoselective homolytic hydrostannylation of allyl and homoallyl alcohols. 
,
-Disubstituted allyl alcohols and ,
-disubstituted homoallyl alcohols were converted into - and 
-stannylated alcohols with high 1,2-syn and 1,3-syn diastereoselectivity, respectively. The origin of the stereochemical outcomes can be rationalized by conformational fixation of the intermediary -stannylalkyl radical by coordination of the hydroxy group to the Lewis acidic tin center.
,-Disubstituted allyl alcohols and ,-disubstituted homoallyl alcohols were converted into - and -stannylated alcohols with high 1,2-syn and 1,3-syn diastereoselectivity, respectively. The origin of the stereochemical outcomes can be rationalized by conformational fixation of the intermediary -stannylalkyl radical by coordination of the hydroxy group to the Lewis acidic tin center.