(5S)-1-aza-2-imino-3-oxa-4,4-diphenylbicyclo(3.3.0)octane:: a novel chiral catalytic source containing the N-(C=NH)-O moiety for the borane-mediated asymmetric reduction of prochiral ketones

被引：6

作者：

Basavaiah, Deevi ^{[1
]}

Rao, Kalapala Venkateswara ^{[1
]}

Reddy, Bhavanam Sekhara ^{[1
]}

机构：

[1] Univ Hyderabad, Sch Chem, Hyderabad 500046, Andhra Pradesh, India

来源：

TETRAHEDRON-ASYMMETRY | 2007年 / 18卷 / 08期

关键词：

D O I：

10.1016/j.tetasy.2007.03.017

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

(5S)- 1-Aza-2-imino-3-oxa-4,4-diphenylbicyclo(3.3.0)octane, a novel chiral catalytic source containing the N-(C=NH)-O moiety, has been synthesized and successfully utilized, for the first time, as a chiral catalytic source in the borane-mediated asymmetric reduction of prochiral ketones in refluxing toluene, to provide the corresponding secondary alcohols with up to 93% enantiomeric excess. (c) 2007 Elsevier Ltd. All rights reserved.

引用

页码：963 / 967

页数：5

共 6 条

[1] (5S)-1,3-Diaza-2-imino-3-phenylbicyclo[3.3.0]octane:: first example of guanidine based in situ recyclable chiral catalytic source for borane-mediated asymmetric reduction of prochiral ketones
Basavaiah, Deevi
Rao, Kalapala Venkateswara
Reddy, Bhavanam Sekhara
TETRAHEDRON-ASYMMETRY, 2006, 17 (07) : 1036 - 1040
[2] Synthesis and Crystal Structure of (2S,5S)-1-Aza-2- (2-pyridyl)-3-oxa-4,4-diphenylbicyclo [3.3.0] Octane
LU Jun JI Shun-Jun② QIAN Rong JIANG Zhao-Qin ZHANG Yong LANG Jian-Ping (School of Chemistry and Chemical Engineering
结构化学, 2004, (06) : 527 - 530
[3] Synthesis and crystal structure of (2S,5S)-1-aza-2-(2-pyridyl)-3-oxa-4,4-diphenylbicyclo [3.3.0] octane
Lu, J
Ji, SJ
Qian, R
Jiang, ZQ
Zhang, Y
Lang, JP
CHINESE JOURNAL OF STRUCTURAL CHEMISTRY, 2004, 23 (06) : 627 - 630
[4] A new chiral catalytic source with an N-P=O structural framework containing a proximal hydroxyl group for the borane-mediated asymmetric reduction of prochiral ketones
Basavaiah, D
Reddy, GJ
Chandrashekar, V
TETRAHEDRON-ASYMMETRY, 2004, 15 (01) : 47 - 52
[5] (2S,5S)-1,3-Diaza-2-phospha-2-oxo-2-chloro-3-phenylbicyclo[3.3.0] octane:: a novel chiral source for borane-mediated catalytic chiral reductions
Basavaiah, D
Reddy, GJ
Chandrashekar, V
TETRAHEDRON-ASYMMETRY, 2002, 13 (11) : 1125 - 1128
[6] A study toward understanding the role of a phosphorus stereogenic center in (5S)-1,3-diaza-2-phospha-2-oxo-3-phenylbicyclo(3.3.0)octane derivatives as catalysts in the borane-mediated asymmetric reduction of prochiral ketones
Basavaiah, D
Chandrashekar, V
Das, U
Reddy, GJ
TETRAHEDRON-ASYMMETRY, 2005, 16 (24) : 3955 - 3962

← 1 →