Catalyst-Controlled Regiodivergent Synthesis of α/β-Dipeptide Derivatives via N-Allylic Alkylation of O-Alkyl Hydroxamates with MBH Carbonates

被引:0
作者
Wang, Shutao [1 ]
Zheng, Lianyou [1 ]
Song, Shaoli [1 ]
Wang, Siyu [1 ]
Zhang, Zhuoqi [1 ]
Xiang, Jinbao [1 ,2 ]
机构
[1] Jilin Univ, Sch Pharmaceut Sci, Ctr Combinatorial Chem & Drug Discovery, Changchun 130021, Peoples R China
[2] Jilin Univ, Sch Life Sci, Key Lab Mol Enzymol & Engn, Minist Educ, Changchun 130021, Peoples R China
基金
中国国家自然科学基金;
关键词
BAYLIS-HILLMAN CARBONATES; AMINO-ACID-DERIVATIVES; BOND-CLEAVAGE; ONE-POT; BETA; PEPTIDES; CYCLIZATION; AMINATION; ANALOGS; GAMMA;
D O I
10.1002/asia.202101186
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A controllable and regiodivergent N-allylation reaction involving readily available O-alkyl hydroxamates derived from natural alpha-amino acids has been developed, allowing regiospecific access to alpha/beta-dipeptides containing aunsaturated beta-amino acids moieties in moderate to good yields. The regioselectivity could be conveniently switched by alternation of the catalysts and solvents.
引用
收藏
页数:9
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共 67 条
[1]  
[Anonymous], 2006, ANGEW CHEM, V118, P1270
[2]  
[Anonymous], 2016, Angew. Chem, V128, P2187
[3]  
[Anonymous], 2009, ANGEW CHEM, V121, P5847
[4]  
[Anonymous], 2018, ANGEW CHEM, V130, P14025
[5]   Recent advances in the Baylis-Hillman reaction and applications [J].
Basavaiah, D ;
Rao, AJ ;
Satyanarayana, T .
CHEMICAL REVIEWS, 2003, 103 (03) :811-891
[6]   Chemical Protein Synthesis with the α-Ketoacid-Hydroxylamine Ligation [J].
Bode, Jeffrey W. .
ACCOUNTS OF CHEMICAL RESEARCH, 2017, 50 (09) :2104-2115
[7]   Chemoselective amide ligations by decarboxylative condensations of N-alkylhydroxylamines and α-ketoacids [J].
Bode, JW ;
Fox, RM ;
Baucom, KD .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (08) :1248-1252
[8]   Peptides Containing β-Amino Acid Patterns: Challenges and Successes in Medicinal Chemistry [J].
Cabrele, Chiara ;
Martinek, Tamas A. ;
Reiser, Oliver ;
Berlicki, Lukasz .
JOURNAL OF MEDICINAL CHEMISTRY, 2014, 57 (23) :9718-9739
[9]   Catalyst-Controlled Divergent Intramolecular Cyclizations of Morita-Baylis-Hillman Carbonates [J].
Cai, Wei ;
He, Yanlin ;
Zhou, Yiming ;
Huang, You .
JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (17) :12267-12276
[10]   Dehydro-β-amino Acid Containing Peptides as Promising Sequences for Drug Development [J].
Cardillo, Giuliana ;
Gennari, Arianna ;
Gentilucci, Luca ;
Mosconi, Elisa ;
Tolomelli, Alessandra ;
Troisi, Stefano .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (34) :5991-5997