Stereoselective Synthesis of Norephedrine and Norpseudoephedrine by Using Asymmetric Transfer Hydrogenation Accompanied by Dynamic Kinetic Resolution

被引：46

作者：

Lee, Hyeon-Kyu ^{[1
,2
]}

Kang, Soyeong ^{[1
]}

Choi, Eun Bok ^{[1
]}

机构：

[1] Korea Res Inst Chem Technol, Bioorgan Sci Div, Taejon 305600, South Korea

[2] Univ Sci & Technol, Taejon 305333, South Korea

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 77卷 / 12期

关键词：

ENANTIOSELECTIVE SYNTHESIS; COMPLEX; KETONES; REDUCTION; ALCOHOLS; OLEFINS; PURE;

D O I：

10.1021/jo300867y

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Each of the enantiomers of both norephedrine and norpseudoephedrine were stereoselectively prepared from the common, prochiral cyclic sulfamidate imine of racemic 1-hydroxy-1-phenyl-propan-2-one by employing asymmetric transfer hydrogenation (ATH) catalyzed by the well-defined chiral Rh-complexes, (S,S)- or (R,R)-Cp*RhCl(TsDPEN), and HCO2H/Et3N as the hydrogen source. The ATH processes are carried out under mild conditions (rt, 15 min) and are accompanied by dynamic kinetic resolution.

引用

页码：5454 / 5460

页数：7

共 50 条

[1] Catalytic asymmetric transfer hydrogenation/dynamic kinetic resolution: an efficient synthesis of florfenicol
Wang, Xinlong
Xu, Lingjun
Yan, Lingjie
Wang, Haifeng
Han, Sheng
Wu, Yan
Chen, Fener
[J]. TETRAHEDRON, 2016, 72 (14) : 1787 - 1793
[2] Dynamic Kinetic Resolution Approach for the Asymmetric Synthesis of Tetrahydrobenzodiazepines Using Transfer Hydrogenation by Chiral Phosphoric Acid
Horiguchi, Kosaku
Yamamoto, Eri
Saito, Kodai
Yamanaka, Masahiro
Akiyama, Takahiko
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (24) : 8078 - 8083
[3] Asymmetric Transfer Hydrogenation: Dynamic Kinetic Resolution of α-Amino Ketones
Gediya, Shweta K.
Clarkson, Guy J.
Wills, Martin
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (17): : 11309 - 11330
[4] Dynamic kinetic resolution in the stereoselective synthesis of 4,5-diaryl cyclic sulfamidates by using chiral rhodium-catalyzed asymmetric transfer hydrogenation
Han, Juae
Kang, Soyeong
Lee, Hyeon-Kyu
[J]. CHEMICAL COMMUNICATIONS, 2011, 47 (13) : 4004 - 4006
[5] STEREOSELECTIVE HYDROGENATION VIA DYNAMIC KINETIC RESOLUTION
NOYORI, R
IKEDA, T
OHKUMA, T
WIDHALM, M
KITAMURA, M
TAKAYA, H
AKUTAGAWA, S
SAYO, N
SAITO, T
TAKETOMI, T
KUMOBAYASHI, H
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (25) : 9134 - 9135
[6] Dynamic kinetic resolution of racemic α-sulfonylaldehydes via asymmetric transfer hydrogenation
Wu, Guofeng
Zhu, Jinlong
Ding, Zhenhua
Shen, Zongxuan
Zhang, Yawen
[J]. TETRAHEDRON LETTERS, 2009, 50 (04) : 427 - 429
[7] Dynamic Kinetic Resolution of β-Substituted α-Diketones via Asymmetric Transfer Hydrogenation
Chen, Ting
Liu, Wenjun
Gu, Wei
Niu, Shengtong
Lan, Shouang
Zhao, Zhifei
Gong, Fan
Liu, Jinggong
Yang, Shuang
Cotman, Andrej Emanuel
Song, Jinshuai
Fang, Xinqiang
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2023, 145 (01) : 585 - 599
[8] Dynamic Kinetic Resolution of β-Cyano α-Ketoesters via Asymmetric Transfer Hydrogenation
Hu, Ruiyu
Wang, Fangyuan
Pan, Fan
Ratovelomanana-Vidal, Virginie
Chen, Gen-Qiang
Li, Xiuxiu
Zhang, Xumu
[J]. ORGANIC LETTERS, 2024, 26 (35) : 7457 - 7462
[9] Dynamic Kinetic Resolution of α-Keto Esters via Asymmetric Transfer Hydrogenation
Steward, Kimberly M.
Gentry, Emily C.
Johnson, Jeffrey S.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (17) : 7329 - 7332
[10] Dynamic kinetic resolution of β-keto sulfones via asymmetric transfer hydrogenation
Ding, Zhenhua
Yang, Jin
Wang, Ting
Shen, Zongxuan
Zhang, Yawen
[J]. CHEMICAL COMMUNICATIONS, 2009, (05) : 571 - 573

← 1 2 3 4 5 →