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.
Department of Chemistry, 21st Century COE, Graduate School of Pure and Applied Sciences, University of Tsukuba, and CREST, Japan.
Katsukiyo
K
Miura
Di
D
Wang
Akira
A
Hosomi