57256-12-9Relevant academic research and scientific papers
Directive effect of the 2- and 3-axial hydroxy groups that appeared in the complex metal hydride reduction of cyclohexanones
Senda,Kikuchi,Inui,Itoh
, p. 237 - 242 (2007/10/03)
A directive effect of the 2-axial hydroxy group appeared in the LiAlH4, NaBH4, and Zn(BH4)2 reduction of cyclohexanone, while the 3-axial hydroxy group exhibited a steric hindrance. The distance between the carbonyl carbon and the hydroxy group interacting with the hydride reagent was responsible for such a difference. In the reduction of Na[B(OAc)3H], the 2- and 3-axial hydroxycyclohexanones gave the products obtained by the hydride approaching from the side of the hydroxy group. The key point of the stereoselectivity was the formation of Na[B(OAc)2(OR)H, which was more reactive than the parent hydride, by exchanging the acetate ion with the alkoxide. Although the reduction was performed under the condition that the hydride/substrate ratio was 1, the conversion of the hydroxy ketone to an alcohol were 4, NaBH4, and Zn(BH4)2 reductions in tetrahydrofuran. The conversions in the NaBH4 reduction in ethanol were > 90%.
The Regiochemistry and Stereochemistry of the Hydroboration of Allylsilanes
Fleming, Ian,Lawrence, Nicholas J.
, p. 3309 - 3326 (2007/10/02)
The hydroboration of a wide range of allylsilanes 3 and 5-21 is found to be generally regioselective for attachment of the boron to C-3 and hydrogen to C-2 of the allyl unit, and to be generally stereoselective in the sense 1, with attachment of the boron
Syntheses and Conformational Properties of Stereoisomeric 1,3-Cyclohexanediol and 3-Aminocyclohexanol Derivatives. X-Ray Structure Analysis of trans-1,3-Dihydroxy-1,5,5-trimethylcyclohexane and c-3-Amino-r-1-hydroxy-1,5,5-trimethylcyclohexane
Nader, Franz W.,Heinrich, Wolfgang,Baar-Schaefer, Monika,Hangel, Elfriede
, p. 4314 - 4329 (2007/10/02)
Solvomercuration of cyclohexenols 3 and 4 yields the respective cis/trans-diols 1a and pure trans-diol 2a.Via the monotosylates the analogous cis-diol cis-2a as well as the cis-amino alcohols cis-1b and cis-2b are prepared diastereomerically pure in good
