[HTML][HTML] Stereoselective sodium borohydride reductions of cyclopentanones: influence of ceric chloride on the stereochemistry of reaction

MG Constantino, LGO Matias, GVJ Silva, E Barbieri… - Química …, 1998 - SciELO Brasil
In this paper we describe the reduction by NaBH4 of some cyclopentanones containing an
oxygenated function at the side chain position beta to the carbonyl group, both in the …

Kinetics, stereochemistry, and mechanism of the sodium borohydride reduction of alkyl-substituted cyclohexanones

B Rickborn, MT Wuesthoff - Journal of the American Chemical …, 1970 - ACS Publications
The previously used method for determining the kinetics of sodium borohydride reduction of
cyclo-hexanones was shown to be inadequate, giving rise to small errors leading to …

Studies toward the diastereoselective reduction of 2-alkoxycarbonyl-2-allyl-cyclopentanone derivatives with boron hydrides

CAM Fraga, EJ Barreiro - Synthetic communications, 1995 - Taylor & Francis
Abstract The reduction of 2-alkoxycarbonyl-2-allyl-cyclopentanone derivatives with
inexpensive boron hydrides were studied showing that this process depend on chelation …

Stereoelectronic influence on the NaBH4 reduction stereoselectivity of alicyclic β-ketoesters

C Beeson, N Pham, TA Dix - Tetrahedron letters, 1992 - Elsevier
The stereochemistry of β-hydroxyesters produced in the NaBH 4 reduction of alicyclic β-
ketoesters has been determined. An enhanced rate of reduction has been observed for …

The kinetic role of hydroxylic solvent in the reduction of ketones by sodium borohydride. New proposals for mechanism, transition state geometry, and a comment on …

DC Wigfield, FW Gowland - The Journal of Organic Chemistry, 1977 - ACS Publications
The kinetic order with respect to 2-propanol in the reduction of cyclohexanone by sodium
borohydride is found to be 1.5, and an acyclic mechanism is proposed; in consequence of …

Limited alkoxy group exchange in tetraalkoxyborohydrides: Evidence against the four-centre transition state in the borohydride reduction of ketones

DC Wigfield, FW Gowland - Tetrahedron Letters, 1976 - Elsevier
Since the discovery of sodium borohydride by Schlesinger, Brown and co-workers. 1 its use
in the reduction of ketones has presented the organic chemist with a continual series of …

1, 3-syn diastereoselective reduction of β-hydroxyketones utilizing alkoxydialkylboranes

KM Chen, GE Hardtmann, K Prasad, O Repič… - Tetrahedron …, 1987 - Elsevier
Tetrahedron Letters,Vol.28,No.2,pp 155-158,1987 Printed in Great Britain 0040-4039/87 $3.00 +
.OO Pergamon Journals Ltd. Kau-Min Page 1 Tetrahedron Letters,Vol.28,No.2,pp 155-158,1987 …

Studies on diastereoselective reduction of cyclic β-ketoesters with boron hydrides. Part 4: The reductive profile of functionalized cyclohexanone derivatives

CAM Fraga, LHP Teixeira, CM de S Menezes… - Tetrahedron, 2004 - Elsevier
Reduction of 2-allyl-2-carboalkoxycyclohexanones (), 2-propyl-2-
carboethoxycyclohexanone () and 2-benzyl-2-carboethoxycyclohexanone () with boron …

Unexpected Selectivity in Sodium Borohydride Reductions of α‐Substituted Esters: Experimental and Theoretical Studies

LC Li, JX Jiang, J Ren, Y Ren, CU Pittman Jr, HJ Zhu - 2006 - Wiley Online Library
The propensity of sodium borohydride to reduce the carbonyl group in eleven α‐substituted
and two aromatic esters has been investigated by experiments and at the B3LYP/6‐31++ G …

Reduction of ketones by sodium borohydride in the absence of protic solvents. Inter versus intramolecular mechanism

MM Kayser, S Eliev, O Eisenstein - Tetrahedron Letters, 1983 - Elsevier
4 R,CO + BHGO --- tR2CH0)4B@ - H20 4 R,CHOH Page 1 Tetrahedron Letters,Vol.24,No.lO,pp
1015-1018,1983 0040-4039/83/101015-04$03.0@/0 Printed in Creat Britain 01983 Pergamon …