Rhodium-Catalyzed Highly Regio- and Enantioselective Hydrogenation of Tetrasubstituted Allenyl Sulfones: An Efficient Access to Chiral Allylic Sulfones

被引：33

作者：

Long, Jiao ^{[1
,2
]}

Shi, Liyang ^{[1
,2
]}

Li, Xiong ^{[1
,2
]}

Lv, Hui ^{[1
,2
,5
]}

Zhang, Xumu ^{[3
,4
]}

机构：

[1] Wuhan Univ, Key Lab Biomed Polymers, Minist Educ, Wuhan 430072, Hubei, Peoples R China

[2] Wuhan Univ, Coll Chem & Mol Sci, Wuhan 430072, Hubei, Peoples R China

[3] Southern Univ Sci & Technol, Dept Chem, Shenzhen 518055, Guangdong, Peoples R China

[4] Southern Univ Sci & Technol, Shenzhen Grubbs Inst, Shenzhen 518055, Guangdong, Peoples R China

[5] Wuhan Univ, Engn Res Ctr Organosilicon Cpds & Mat, Minist Educ, Coll Chem & Mol Sci, Wuhan 430072, Hubei, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2018年 / 57卷 / 40期

基金：

中国国家自然科学基金;

关键词：

allenes; allylic sulfone; asymmetric hydrogenation; enantioselectivity; rhodium; BETA-ACYLAMINO NITROOLEFINS; ASYMMETRIC HYDROGENATION; ALPHA; BETA-UNSATURATED KETONES; AMINO NITROALKANES; GENERAL-APPROACH; ENAMIDO ESTERS; OLEFINS; LIGANDS; ACIDS; SEMIHYDROGENATION;

D O I：

10.1002/anie.201804891

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A highly regio- and enantioselective hydrogenation of challenging tetrasubstituted allenyl sulfones has been developed, affording chiral allylic sulfones in good yields with excellent regio- and enantioselectivities (up to 99% yield and 99% ee). This method provides an efficient and concise route to chiral allylic sulfones, thus offering an atom-economic process with a wide range of potential applications in organic synthesis and medicinal chemistry.

引用

页码：13248 / 13251

页数：4

共 50 条

[1] Rhodium-Catalyzed Highly Enantioselective Hydrogenation of a Tetrasubstituted Enamine
Yamada, Masatoshi
Kato, Tomoaki
Ikemoto, Tomomi
Yamano, Mitsuhisa
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2021, 25 (04) : 1074 - 1079
[2] Rhodium-Catalyzed Chemodivergent Regio- and Enantioselective Allylic Alkylation of Indoles
Sun, Minghe
Liu, Min
Li, Changkun
CHEMISTRY-A EUROPEAN JOURNAL, 2021, 27 (10) : 3457 - 3462
[3] Regio- and Enantioselective Preparation of Chiral Allylic Sulfones Featuring Elusive Quaternary Stereocenters
Cai, Aijie
Kleij, Arjan W.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (42) : 14944 - 14949
[4] Rhodium-Catalyzed Regio- and Enantioselective Allylic Sulfonylation from Sulfonyl Hydrazides
Rehman, Sajid Ur
Li, Changkun
ORGANIC LETTERS, 2023, 25 (20) : 3693 - 3697
[5] Highly Efficient Enantioselective Synthesis of Chiral Sulfones by Rh-Catalyzed Asymmetric Hydrogenation
Yan, Qiaozhi
Xiao, Guiying
Wang, Ying
Zi, Guofu
Zhang, Zhanbin
Hou, Guohua
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (04) : 1749 - 1756
[6] Enantioselective Synthesis of Allylic Sulfones via Rhodium-Catalyzed Direct Hydrosulfonylation of Allenes and Alkynes
Chang, Chieh-Yu
Aponick, Aaron
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2024, 146 (25) : 16996 - 17002
[7] Rh-Catalyzed Asymmetric Hydrogenation of a-Substituted Alkenyl Sulfones: Highly Chemo- and Enantioselective Access to Chiral Sulfones
Wu, Xiaoxue
Su, Yanhao
Zi, Guofu
Ye, Weiping
Hou, Guohua
ORGANIC LETTERS, 2023, 25 (37) : 6858 - 6862
[8] Nickel-Catalyzed Highly Enantioselective Hydrogenation of β-Acetylamino Vinylsulfones: Access to Chiral β-Amido Sulfones
Long, Jiao
Gao, Wenchao
Guan, Yuqing
Lv, Hui
Zhang, Xumu
ORGANIC LETTERS, 2018, 20 (18) : 5914 - 5917
[9] Rhodium-Catalyzed Regio- and Enantioselective Addition of N-Hydroxyphthalimide to Allenes: A Strategy To Synthesize Chiral Allylic Alcohols
Liu, Zi
Breit, Bernhard
ORGANIC LETTERS, 2018, 20 (01) : 300 - 303
[10] Rhodium-Catalyzed Asymmetric Hydrogenation of Tetrasubstituted α,β-Unsaturated Amides: Efficient Access to Chiral β-Amino Amides
Jiao, Bing
Wang, Fangyuan
Lv, Hui
CHINESE JOURNAL OF CHEMISTRY, 2024,

← 1 2 3 4 5 →