162660-49-3Relevant academic research and scientific papers
Highly diastereoselective hydrostannylation of allyl and homoallyl alcohols with dibutyl(trifluoromethanesulfoxy)stannane
Miura, Katsukiyo,Wang, Di,Hosomi, Akira
, p. 9366 - 9367 (2007/10/03)
Dibutyl(trifluoromethanesulfoxy)stannane (Bu2Sn(OTf)H, 1a) was found to be very valuable for highly diastereoselective homolytic hydrostannylation of allyl and homoallyl alcohols. α,β-Disubstituted allyl alcohols and α,γ-disubstituted homoallyl alcohols were converted into γ- and δ-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 β-stannylalkyl radical by coordination of the hydroxy group to the Lewis acidic tin center. Copyright
Hydroxy-directed Reduction of β-Hydroxycycloalkanones as a Stereoselective Route to 1,3-Diols: X-Ray Crystal Structure and Structural Features of (1R*,2R*,6S*)-2-cyclopentanol
Thompson, Stephen H. J.,Mahon, Mary F.,Molloy, Kieran C.,Hadley, Michael S.,Gallagher, Timothy
, p. 379 - 384 (2007/10/02)
syn and anti Alcohol adducts 4/5 and 6/7 undergo reduction using NaBH(OAc)3 to give 1,3-diols with good to excellent levels of diastereoselectivity.Reduction using NaBH4 is generally less selective but, in the cyclohexyl series, reduction of the syn aldol
