Multiple Absolute Stereocontrol in Cascade Lactone Formation via Dynamic Kinetic Resolution Driven by the Asymmetric Transfer Hydrogenation of Keto Acids with Oxo-Tethered Ruthenium Catalysts

被引：42

作者：

Touge, Taichiro ^{[1
]}

Sakaguchi, Kazuhiko ^{[1
]}

Tamaki, Nao ^{[1
]}

Nara, Hideki ^{[1
]}

Yokozawa, Tohru ^{[1
]}

Matsumura, Kazuhiko ^{[1
]}

Kayaki, Yoshihito ^{[2
]}

机构：

[1] Takasago Int Corp, Corp Res & Dev Div, 1-4-11 Nishi Yawata, Hiratsuka, Kanagawa 2540073, Japan

[2] Tokyo Inst Technol, Dept Chem Sci & Engn, Sch Mat & Chem Technol, Meguro Ku, O Okayama 2-12-1-E4-1, Tokyo 1528552, Japan

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2019年 / 141卷 / 41期

关键词：

LIGAND BIFUNCTIONAL CATALYSIS; CHARACTER IMPACT ODORANTS; AROMATIC KETONES; REDUCTION; ALCOHOLS; INTERMEDIATE; MECHANISM; ESTERS; ROUTE;

D O I：

10.1021/jacs.9b07297

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A straightforward asymmetric construction of chiral fused gamma- and delta-lactones containing multiple contiguous stereocenters was successfully developed by either (1) the dynamic kinetic resolution-asymmetric transfer hydrogenation (DKR-ATH) reaction using oxo-tethered Ru(II) complexes followed by syn-selective lactonization or (2) the tandem DKR-ATH/lactonization in combination with asymmetric hydrogenation catalyzed by Ru-chiral diphosphine complexes. The expedient protocol is applicable to the enantioselective synthesis of natural wine lactone and a biologically active benzo-fused lactone with an unprecedented level of diastereo- and enantioselectivity.

引用

页码：16354 / 16361

页数：8

共 14 条

[1] Selective Asymmetric Transfer Hydrogenation of α-Substituted Acetophenones with Bifunctional Oxo-Tethered Ruthenium(II) Catalysts
Yuki, Yamato
Touge, Taichiro
Nara, Hideki
Matsumura, Kazuhiko
Fujiwhara, Mitsuhiko
Kayaki, Yoshihito
Ikariya, Takao
ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (03) : 568 - 574
[2] Convincing Catalytic Performance of Oxo-Tethered Ruthenium Complexes for Asymmetric Transfer Hydrogenation of Cyclic α-Halogenated Ketones through Dynamic Kinetic Resolution
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Nara, Hideki
Kida, Michio
Matsumura, Kazuhiko
Kayaki, Yoshihito
ORGANIC LETTERS, 2021, 23 (08) : 3070 - 3075
[3] Efficient Access to Chiral Benzhydrols via Asymmetric Transfer Hydrogenation of Unsymmetrical Benzophenones with Bifunctional Oxo-Tethered Ruthenium Catalysts
Touge, Taichiro
Nara, Hideki
Fujiwhara, Mitsuhiko
Kayaki, Yoshihito
Ikariya, Takao
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (32) : 10084 - 10087
[4] Dynamic Kinetic Resolution of α-Keto Esters via Asymmetric Transfer Hydrogenation
Steward, Kimberly M.
Gentry, Emily C.
Johnson, Jeffrey S.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (17) : 7329 - 7332
[5] Dynamic kinetic resolution of β-keto sulfones via asymmetric transfer hydrogenation
Ding, Zhenhua
Yang, Jin
Wang, Ting
Shen, Zongxuan
Zhang, Yawen
CHEMICAL COMMUNICATIONS, 2009, (05) : 571 - 573
[6] Asymmetric Transfer Hydrogenation of α-Substituted-β-Keto Carbonitriles via Dynamic Kinetic Resolution
Wang, Fangyuan
Yang, Tilong
Wu, Ting
Zheng, Long-Sheng
Yin, Congcong
Shi, Yongjie
Ye, Xiang-Yu
Chen, Gen-Qiang
Zhang, Xumu
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2021, 143 (06) : 2477 - 2483
[7] Dynamic Kinetic Resolution of α-Keto Esters via Asymmetric Transfer Hydrogenation (vol 134, pg 7329, 2012)
Steward, Kimberly M.
Gentry, Emily C.
Johnson, Jeffrey S.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (10) : 3715 - 3715
[8] Stereopure Functionalized Benzosultams via Ruthenium(II)-Catalyzed Dynamic Kinetic Resolution-Asymmetric Transfer Hydrogenation
Jeran, Marko
Cotman, Andrej Emanuel
Stephan, Michel
Mohar, Barbara
ORGANIC LETTERS, 2017, 19 (08) : 2042 - 2045
[9] Ru-catalyzed asymmetric transfer hydrogenation of racemic /3-keto γ-lactams via dynamic kinetic resolution
Malekar, Pushpa, V
More, Ganesh, V
Ramana, Chepuri, V
TETRAHEDRON, 2024, 167
[10] Establishment of the Continuous Synthesis of Ceramide(D-erythro-CER[NDS]) via Oxo-Tethered Ruthenium Complex-Catalyzed Asymmetric Transfer Hydrogenation Using Pipe-Flow Reactor
Kuwana, Masahiro
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Saito, Takao
JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2020, 78 (12) : 1184 - 1194

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