50648-71-0Relevant academic research and scientific papers
Nickel-catalyzed borylative ring opening of vinyl epoxides and aziridines
Crotti, Stefano,Bertolini, Ferruccio,Macchia, Franco,Pineschi, Mauro
, p. 3762 - 3765 (2011/03/19)
Image Presented A mild ring opening of vinyl epoxides and aziridines with B2Pin2 catalyzed by Ni(0)-Binap affords new functionalized allylic boron derivatives which undergo sequential transformations. The uncatalyzed allylation of al
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
Tandem aldol-reduction reaction of dimethylsilyl enolates: A new method for stereoselective preparation of 1,3-diols
Miura, Katsukiyo,Nakagawa, Takahiro,Suda, Shuntaro,Hosomi, Akira
, p. 150 - 151 (2007/10/03)
In the presence of a catalytic amount of TBAF (Bu4NF), dimethylsilyl enolates derived from acyclic ketones reacted with aldehydes to give syn,syn-1,3-diols 7a and 8a with moderate to high diastereoselectivity. The stereochemical outcome can be attributed to a syn-selective aldol reaction and the subsequent 1,2-syn-selective intramolecular reduction.
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
STEREOSELECTIVITY IN THE HYDROBORATION OF CHIRAL CYCLOHEXANE-DERIVED ALLYLIC ALCOHOLS
Birtwistle, David H.,Brown, John M.,Foxton, Michael W.
, p. 4367 - 4370 (2007/10/02)
The isomeric 2-ethylidenecyclohexanols are hydroborated by t-hexylborane with weak stereoselectivity whilest 1-(1'-hydroxyalkyl)cyclohexenes show up to 50:1 discrimination.
Synthesis and Configurational and Conformational Study of the Diastereomeric 2-(α-Hydroxybenzyl)- and 2-(α-Methoxybenzyl)-cyclohexanols and Some of Their Derivatives
Balsamo, Aldo,Crotti, Paolo,Macchia, Franco
, p. 3065 - 3071 (2007/10/02)
All the diastereomeric 2-(α-hydroxybenzyl)-(3), (4), (13), and (14) and 2-(α-methoxybenzyl)cyclohexanols (5), (6), (15), and (16) have been synthesized and some of their derivatives prepared as model compounds of the products of ring opening of some cyclo
