Asymmetric borane reduction of prochiral ketones catalyzed by α,α-disubstituted aziridinemethanols

被引：3

作者：

Xu, Wenjin ^{[1
]}

Guo, Hao ^{[1
]}

Zhu, Qifeng ^{[1
]}

Ke, Xianbing ^{[1
]}

Hu, Xianming ^{[1
]}

机构：

[1] Wuhan Univ, Coll Pharm, State Key Lab Virol, Wuhan 430072, Peoples R China

来源：

CATALYSIS LETTERS | 2008年 / 125卷 / 3-4期

关键词：

asymmetric reduction; prochiral ketones; aziridinemethanol; secondary alcohol;

D O I：

10.1007/s10562-008-9558-6

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

A series of novel alpha,alpha-disubstituted aziridinemethanols have been developed for the enantioselective reduction of ketones in refluxing tetrahydrofuran. The optically active secondary alcohol products were obtained in good enantiomeric excess (similar to 96.8%) and excellent yields. The results showed that the substituent groups on the hydroxyl-bearing carbon of aziridinemethanols obviously affected the enantioselectivity.

引用

页码：302 / 307

页数：6

共 50 条

[1] Asymmetric Borane Reduction of Prochiral Ketones Catalyzed by α,α-Disubstituted Aziridinemethanols
Wenjin Xu
Hao Guo
Qifeng Zhu
Xianbing Ke
Xianming Hu
Catalysis Letters, 2008, 125 : 302 - 307
[2] Asymmetric reduction of acetophenone using α,α-disubstituted aziridinemethanols and borane
Xu, Wenjin
Guo, Hao
Zhang, Jun
Zhu, Qifeng
Hu, Xianming
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2009, 300 (1-2) : 25 - 28
[3] Asymmetric borane reduction of prochiral ketones catalyzed by 4-substituted prolinol
Zhang, YW
Liang, J
Lu, J
Guo, CL
Shen, ZX
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2000, 20 (03) : 334 - 337
[4] Asymmetric borane reduction of prochiral ketones catalyzed by C3-symmetric sulfonamide
Li, Gao-Qiang
Yan, Ze-Yi
Niu, Yan-Ning
Wu, Lu-Yong
Wei, Hai-Long
Liang, Yong-Min
TETRAHEDRON-ASYMMETRY, 2008, 19 (07) : 816 - 821
[5] Diphenylamine-derived bis-hydroxyamide catalyzed asymmetric borane reduction of prochiral ketones
Wang, Jin
Liu, Han
Du, Da-Ming
TETRAHEDRON-ASYMMETRY, 2009, 20 (05) : 605 - 609
[6] Asymmetric borane reduction of prochiral ketones catalyzed by phosphinamides prepared from L-serine
Li, KY
Zhou, ZH
Wang, LX
Zhao, GF
Choi, MCK
Zhou, QL
Tang, CC
HETEROATOM CHEMISTRY, 2003, 14 (03) : 288 - 291
[7] ASYMMETRIC BORANE REDUCTION OF KETONES CATALYZED BY OXAZABOROLIDINE
YOUN, IK
LEE, SW
PAK, CS
TETRAHEDRON LETTERS, 1988, 29 (35) : 4453 - 4456
[8] Catalytic asymmetric borane reduction of prochiral ketones by the use of chiral β-diamines
Asami, M
Sato, S
Watanabe, H
CHEMISTRY LETTERS, 2000, (09) : 990 - 991
[9] Enantioselective borane reduction of prochiral aryl ketones catalyzed by camphyl aminoalcohols
Chang, QF
Xu, XY
Yang, XJ
You, TP
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2005, 25 (06) : 669 - 672
[10] Asymmetric borane reduction of prochiral ketones by polymer-supported chiral sulfonamides
Hu, JB
Zhao, G
Yang, GS
Ding, ZD
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (01): : 303 - 304

← 1 2 3 4 5 →