Diastereodivergent Synthesis of Chiral α-Aminoketones via a Catalytic O-H Insertion/Barnes-Claisen Rearrangement Reaction

被引:18
作者
Liu, Yun [1 ]
Chen, Yushuang [1 ]
Yihuo, Aying [1 ]
Zhou, Yuqiao [1 ]
Liu, Xiaohua [1 ]
Lin, Lili [1 ]
Feng, Xiaoming [1 ]
机构
[1] Sichuan Univ, Coll Chem, Minist Educ, Key Lab Green Chem & Technol, Chengdu 610064, Peoples R China
来源
ACS CATALYSIS | 2022年 / 12卷 / 03期
基金
中国国家自然科学基金;
关键词
acceptor/acceptor carbenoid; Barnes-Claisen rearrangement; coordination model; O-H insertion intermediates; diastereodivergent synthesis; mild conditions; ALLYL VINYL ETHERS; ONE-POT SYNTHESIS; STEREOCONTROLLED SYNTHESIS; TERMINAL ALKYNES; RHODIUM; 1-SULFONYL-1,2,3-TRIAZOLES; N-SULFONYL-1,2,3-TRIAZOLE; TRANSANNULATION; DERIVATIVES; CYCLIZATION;
D O I
10.1021/acscatal.1c05789
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
A tandem asymmetric catalytic O-H insertion/Barnes-Claisen rearrangement reaction from 4-acyl-1-sulfonyl-1,2,3-triazoles with allylic alcohols is developed for the purpose of synthesizing all possible stereomers of alpha-aminoketones under mild conditions. It is found that 4-acyl-1-sulfonyl-1,2,3-triazoles not only form rhodium carbenoids with higher electrophilicity under milder conditions in comparison to 4-aryl-1-sulfonyl-1,2,3-triazoles but also afford another coordination model during the N,N'-dioxide/metal complex promoted asymmetric Barnes-Claisen rearrangement. In addition, two different O-H insertion intermediates have been separated and their transformations have been researched. On the basis of control experiments and previous works, a possible mechanism is proposed to illustrate the reaction process and the induction of the stereoselectivity.
引用
收藏
页码:1784 / 1790
页数:7
相关论文
共 70 条
[1]   Highly enantioselective catalytic asymmetric Claisen rearrangement of 2-alkoxycarbonyl-substituted allyl vinyl ethers [J].
Abraham, L ;
Körner, M ;
Hiersemann, M .
TETRAHEDRON LETTERS, 2004, 45 (18) :3647-3650
[2]  
Abraham L, 2001, ANGEW CHEM INT EDIT, V40, P4700, DOI 10.1002/1521-3773(20011217)40:24<4700::AID-ANIE4700>3.0.CO
[3]  
2-6
[4]   Chemoselectivity Switching in the Rhodium-Catalyzed Reactions of 4-Substituted-1-sulfonyl-1,2,3-triazoles with Allenols: Noticeable Differences between 4-Acyl- and 4-Aryl-Triazoles [J].
Alcaide, Benito ;
Almendros, Pedro ;
Fernandez, Israel ;
Martinez del Campo, Teresa ;
Palop, Guillermo ;
Toledano-Pinedo, Mireia ;
Delgado-Martinez, Patricia .
ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (05) :1160-1165
[5]   Recent Advances in Transition-Metal-Catalyzed Denitrogenative Transformations of 1,2,3-Triazoles and Related Compounds [J].
Anbarasan, Pazhamalai ;
Yadagiri, Dongari ;
Rajasekar, Shanmugam .
SYNTHESIS-STUTTGART, 2014, 46 (22) :3004-3023
[6]   Aza-Bellu-Claisen Rearrangement-Enabled Synthesis of Racemic Tapentadol and Its Stereoisomers [J].
Bai, Donghu ;
Huang, Sha-Hua ;
Lin, Zuming ;
Yang, Lin ;
Dai, Junzeng ;
Huang, Meng-Yuan ;
Jia, Xueshun ;
Hong, Ran .
CHINESE JOURNAL OF CHEMISTRY, 2013, 31 (03) :317-320
[7]   CLAISEN REARRANGEMENT OF ALLYL ETHERS OF ALPHA-HYDROXYBENZALACETOPHENONES [J].
BARNES, RP ;
CHIGBO, FE .
JOURNAL OF ORGANIC CHEMISTRY, 1963, 28 (06) :1644-&
[8]   Catalytic Asymmetric Claisen Rearrangement of Gosteli-Type Allyl Vinyl Ethers: Total Synthesis of (-)-9,10-Dihydroecklonialactone B [J].
Becker, Julia ;
Butt, Lena ;
von Kiedrowski, Valeska ;
Mischler, Elisabeth ;
Quentin, Florian ;
Hiersemann, Martin .
JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (07) :3040-3051
[9]   Rhodium(II)-Catalyzed Stereocontrolled Synthesis of 2-Tetrasubstituted Saturated Heterocycles from 1-Sulfonyl-1,2,3-triazoles [J].
Boyer, Alistair .
ORGANIC LETTERS, 2014, 16 (22) :5878-5881
[10]   Transition-Metal-Catalyzed Denitrogenative Transannulation: Converting Triazoles into Other Heterocyclic Systems [J].
Chattopadhyay, Buddhadeb ;
Gevorgyan, Vladimir .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (04) :862-872