Highly regio- and stereoselective hydrostannylation of alkynols with a new Lewis acidic hydrostannane.
[reaction: see text] Bu2Sn(OTf)H (1a), easily prepared from Bu2SnH2 and TfOH, was found to be very valuable for highly regio- and stereoselective hydrostannylation of various propargyl alcohols leading to (Z)-gamma-stannylated allyl alcohols. The stannylation with 1a is applicable to the synthesis of hydroxy-substituted (Z)-vinylstannanes from terminal alkynes bearing a hydroxy group at the homoallylic or bishomoallylic position. The coordination of the hydroxy group to the Lewis acidic tin center plays an important role for the observed regio- and stereochemistry.
Miura
Katsukiyo
K
Department of Chemistry, 21st Century COE, Graduate School of Pure and Applied Sciences, University of Tsukuba, Tsukuba, Ibaraki 305-8571, Japan.
Wang
Di
D
Matsumoto
Yukihiro
Y
Hosomi
Akira
A
D000498:Allyl Compounds / Q000737:chemistry; D017665:Hydroxyl Radical; D013058:Mass Spectrometry; D009947:Organotin Compounds / Q000737:chemistry*; D013055:Spectrophotometry, Infrared; D013237:Stereoisomerism; D014753:Vinyl Compounds / Q000737:chemistry
D000498:Allyl Compounds; D009947:Organotin Compounds; D014753:Vinyl Compounds; C510267:hydrostannane; D017665:Hydroxyl Radical