Rhodium-catalyzed regio- and enantioselective allylic alkylation of pyrazol-5-ones with alkynes

被引：15

作者：

Ji, Ding-Wei ^{[1
,2
]}

Yang, Fan ^{[1
]}

Chen, Bing-Zhi ^{[1
,2
]}

Min, Xiang-Ting ^{[1
,2
]}

Kuai, Chang-Sheng ^{[1
]}

Hu, Yan-Cheng ^{[1
]}

Chen, Qing-An ^{[1
]}

机构：

[1] Chinese Acad Sci, Dalian Inst Chem Phys, Dalian 116023, Peoples R China

[2] Univ Chinese Acad Sci, Beijing 100049, Peoples R China

来源：

CHEMICAL COMMUNICATIONS | 2020年 / 56卷 / 60期

基金：

中国国家自然科学基金;

关键词：

C-C; PRIMARY ALCOHOLS; TERMINAL ALKYNES; PALLADIUM; ALLYLATION; ACID; REGIOSELECTIVITY; HYDROAMINATION; INDOLES; KETONES;

D O I：

10.1039/d0cc04002a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A rhodium-catalyzed asymmetric allylic alkylation of pyrazol-5-ones with internal alkynes is illustrated. In the presence of a chiral rhodium-hydride catalyst, functionalized heterocyclic products bearing an all-carbon quaternary stereogenic center were obtained in high yields with satisfactory enantioselectivities. This protocol also features good regiocontrol and a high atom economy without stoichiometric by-product formation.

引用

页码：8468 / 8471

页数：4

共 50 条

[11] Rhodium-catalyzed regio- and stereoselective addition of diphenylphosphine oxide to alkynes
Han, LB
Zhao, CQ
Tanaka, M
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (17): : 5929 - 5932
[12] Chemo-, Regio-, and Enantioselective Rhodium-Catalyzed Allylation of Triazoles with Internal Alkynes and Terminal Allenes
Berthold, Dino
Breit, Bernhard
ORGANIC LETTERS, 2018, 20 (03) : 598 - 601
[13] Rhodium-Catalyzed Regio- and Enantioselective Direct Allylation of Methyl Ketones
Li, Bing
Li, Changkun
SYNLETT, 2022, 33 (18) : 1863 - 1867
[14] Silicon-oriented regio- and enantioselective rhodium-catalyzed hydroformylation
You, Cai
Li, Xiuxiu
Yang, Yuhong
Yang, Yu-Sheng
Tan, Xuefeng
Li, Shuailong
Wei, Biao
Lv, Hui
Chung, Lung-Wa
Zhang, Xumu
NATURE COMMUNICATIONS, 2018, 9
[15] Silicon-oriented regio- and enantioselective rhodium-catalyzed hydroformylation
Cai You
Xiuxiu Li
Yuhong Yang
Yu-Sheng Yang
Xuefeng Tan
Shuailong Li
Biao Wei
Hui Lv
Lung-Wa Chung
Xumu Zhang
Nature Communications, 9
[16] Regio- and Enantioselective Allylic Alkylation of Terminal Alkynes by Synergistic Rh/Cu Catalysis
Huang, Wen-Yu
Lu, Chun-Hua
Ghorai, Samir
Li, Bing
Li, Changkun
SYNTHESIS-STUTTGART, 2021, 53 (01): : A11 - A14
[17] Regio- and Enantioselective Allylic Alkylation of Terminal Alkynes by Synergistic Rh/Cu Catalysis
Huang, Wen-Yu
Lu, Chun-Hua
Ghorai, Samir
Li, Bing
Li, Changkun
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2020, 142 (36) : 15276 - 15281
[18] Chemo-, regio-, and enantioselective synthesis of allylic nitrones via rhodium-catalyzed addition of oximes to allenes
Wang, Yu-Hsuan
Breit, Bernhard
CHEMICAL COMMUNICATIONS, 2019, 55 (53) : 7619 - 7622
[19] Regio- and Enantiospecific Rhodium-Catalyzed Allylic Substitution with an Acyl Anion Equivalent
Evans, P. Andrew
Oliver, Samuel
ORGANIC LETTERS, 2013, 15 (22) : 5626 - 5629
[20] Rhodium-catalyzed regio- and enantioselective amination of racemic secondary allylic trichloroacetimidates with N-methyl anilines
Arnold, Jeffrey S.
Cizio, Gregory T.
Heitz, Drew R.
Nguyen, Hien M.
CHEMICAL COMMUNICATIONS, 2012, 48 (94) : 11531 - 11533

← 1 2 3 4 5 →