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

[21] Regio- and Diastereoselective Rhodium-Catalyzed Allylic Substitution with Unstabilized Benzyl Nucleophiles
Pal, Debasis
Wright, Timothy B.
O'Connor, Ryan
Evans, P. Andrew
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (06) : 2987 - 2992
[22] Rhodium-catalyzed chemo-, regio-, and enantioselective [2+2+2] cycloaddition of alkynes with isocyanates
Tanaka, K
Wada, A
Noguchi, K
ORGANIC LETTERS, 2005, 7 (21) : 4737 - 4739
[23] Rhodium-Catalyzed Highly Regio- and Enantioselective Hydrogenation of Tetrasubstituted Allenyl Sulfones: An Efficient Access to Chiral Allylic Sulfones
Long, Jiao
Shi, Liyang
Li, Xiong
Lv, Hui
Zhang, Xumu
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (40) : 13248 - 13251
[24] Highly Chemo-, Regio-, and Enantioselective Rhodium-Catalyzed Cross-Cyclotrimerization of Two Different Alkynes with Alkenes
Hara, Jun
Ishida, Mana
Kobayashi, Masayuki
Noguchi, Keiichi
Tanaka, Ken
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (11) : 2956 - 2959
[25] 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
[26] Rh(I)-catalyzed regio- and enantioselective allylic alkylation of Meldrum's acid
Liu, Min
Zhao, Haiying
Li, Changkun
CHINESE CHEMICAL LETTERS, 2021, 32 (01) : 385 - 388
[27] Regio- and stereoselective synthesis of alkenylphosphines: A rhodium-catalyzed hydrophosphination of alkynes using a silylphosphine
Hayashi, Minoru
Matsuura, Yutaka
Watanabe, Yutaka
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (24): : 9248 - 9251
[28] Iridium-catalyzed regio- and enantioselective allylic alkylation of fluorobis(phenylsulfonyl)methane
Liu, Wen-Bo
Zheng, Sheng-Cai
He, Hu
Zhao, Xiao-Ming
Dai, Li-Xin
You, Shu-Li
CHEMICAL COMMUNICATIONS, 2009, (43) : 6604 - 6606
[29] Highly Regio- and Enantioselective Organocatalytic γ-Allylic Alkylation of Quinolines
Meazza, Marta
Rios, Ramon
ADVANCED SYNTHESIS & CATALYSIS, 2021, 363 (05) : 1341 - 1345
[30] Chemo-, Regio-, and Enantioselective Rhodium-Catalyzed Allylation of Pyridazinones with Terminal Allenes
Parveen, Shaista
Li, Changkun
Hassan, Abbas
Breit, Bernhard
ORGANIC LETTERS, 2017, 19 (09) : 2326 - 2329

← 1 2 3 4 5 →