Highly diastereoselective hydrostannylation of allyl and homoallyl alcohols with dibutyl(trifluoromethanesulfoxy)stannane.
Dibutyl(trifluoromethanesulfoxy)stannane (Bu2Sn(OTf)H, 1a) was found to be very valuable for highly diastereoselective homolytic hydrostannylation of allyl and homoallyl alcohols. alpha,beta-Disubstituted allyl alcohols and alpha,gamma-disubstituted homoallyl alcohols were converted into gamma- and delta-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 beta-stannylalkyl radical by coordination of the hydroxy group to the Lewis acidic tin center.
Miura
Katsukiyo
K
Department of Chemistry, 21st Century COE, Graduate School of Pure and Applied Sciences, University of Tsukuba, and CREST, Japan.
Wang
Di
D
Hosomi
Akira
A