One-Pot Synthesis of Novel Chiral β-Amino Acid Derivatives by Enantioselective Mannich Reactions Catalyzed by Squaramide Cinchona Alkaloids

被引：18

作者：

Zhang, Kankan ^{[1
]}

Liang, Xueping ^{[1
]}

He, Ming ^{[1
]}

Wu, Jian ^{[1
]}

Zhang, Yuping ^{[1
]}

Xue, Wei ^{[1
]}

Jin, Linhong ^{[1
]}

Yang, Song ^{[1
]}

Hu, Deyu ^{[1
]}

机构：

[1] Guizhou Univ, State Key Lab Breeding Base Green Pesticide & Agr, Key Lab Green Pesticide & Agr Bioengn, Minist Educ, Guiyang 550025, Peoples R China

来源：

MOLECULES | 2013年 / 18卷 / 06期

基金：

中国国家自然科学基金;

关键词：

Asymmetric Mannich addition; beta-amino acid derivatives; 1,3,4-thiadiazole moiety; thiourea derived from squaramide cinchona alkaloid; STEREOSELECTIVE-SYNTHESIS; ASYMMETRIC-SYNTHESIS; PEPTIDES; ROUTE;

D O I：

10.3390/molecules18066142

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

An efficient one-pot synthesis of novel beta-amino acid derivatives containing a thiadiazole moiety was developed using a chiral squaramide cinchona alkaloid as organocatalyst. The reactions afforded chiral beta-amino acid derivatives in moderate yields and with moderate to excellent enantioselectivities. The present study demonstrated for the first time the use of a Mannich reaction catalyzed by a chiral bifunctional organocatalyst for the one-pot synthesis of novel beta-amino acid derivatives bearing a 1,3,4-thiadiazole moiety on nitrogen.

引用

页码：6142 / 6152

页数：11

共 50 条

[1] Asymmetric Mannich reactions catalyzed by cinchona alkaloid thiourea: enantioselective one-pot synthesis of novel β-amino ester derivatives
Bai, Song
Liang, Xueping
Song, Baoan
Bhadury, Pinaki S.
Hu, Deyu
Yang, Song
TETRAHEDRON-ASYMMETRY, 2011, 22 (05) : 518 - 523
[2] Synthesis of Chiral Chalcone Derivatives Catalyzed by the Chiral Cinchona Alkaloid Squaramide
Xie, Dandan
Xie, Ying
Ding, Yan
Wu, Jian
Hu, Deyu
MOLECULES, 2014, 19 (12) : 19491 - 19500
[3] The Mannich reaction of malonates with simple imines catalyzed by bifunctional cinchona alkaloids:: Enantioselective synthesis of β-amino acids
Song, Jun
Wang, Yi
Deng, Li
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (18) : 6048 - 6049
[4] Enantioselective mannich-type reactions using a novel chiral zirconium catalyst for the synthesis of optically active β-amino acid derivatives
Ishitani, H
Ueno, M
Kobayashi, S
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (34) : 8180 - 8186
[5] CINCHONA ALKALOID THIOUREA-CATALYZED ONE-POT SYNTHESIS AND BIOSELECTIVE ACTIVITIES OF β-AMINO ACID ESTER DERIVATIVES CONTAINING A PYRIMIDINE MOIETY
Bai, Song
Liu, Shan
Zhu, Yunying
Wei, Xian
Zhao, Kunhong
Li, Weihua
Wu, Qin
HETEROCYCLES, 2018, 96 (08) : 1383 - 1397
[6] One-pot synthesis of β-amino acid derivatives from α-amino acids
Saavedra, Carlos J.
Hernandez, Rosendo
Boto, Alicia
Alvarez, Eleuterio
TETRAHEDRON LETTERS, 2006, 47 (49) : 8757 - 8760
[7] Enantioselective one-pot synthesis of 4H-chromene derivatives catalyzed by a chiral Ni(ii) complex
Yu, Xuan
Lan, Wenjie
Li, Jiaqi
Bai, Hui
Qin, Zhaohai
Fu, Bin
RSC ADVANCES, 2020, 10 (72) : 44437 - 44441
[8] Chiral Cinchona Alkaloid-Thiourea Catalyzed Mannich Reaction for Enantioselective Synthesis of ß-Amino Ketones Bearing Benzothiazol Moiety
Lin Peng
Song Baoan
Bhadury, Pinaki S.
Hu Deyu
Zhang Yuping
Jin Linhong
Yang Song
CHINESE JOURNAL OF CHEMISTRY, 2011, 29 (11) : 2433 - 2438
[9] Chiral cinchona alkaloid-derived thiourea catalyst for enantioselective synthesis of novel ß-amino esters by mannich reaction
Li, Weihua
Song, Baoan
Bhadury, Pinaki S.
Li, Liang
Wang, Zhenchao
Zhang, Xiaoyan
Hu, Deyu
Chen, Zhuo
Zhang, Yuping
Bai, Song
Wu, Jian
Yang, Song
CHIRALITY, 2012, 24 (03) : 223 - 231
[10] Iodine catalyzed one-pot synthesis of flavanone and tetrahydropyrimidine derivatives via Mannich type reaction
Kavala, Veerababurao
Lin, Chunchi
Kuo, Chun-Wei
Fang, Hulin
Yao, Ching-Fa
TETRAHEDRON, 2012, 68 (04) : 1321 - 1329

← 1 2 3 4 5 →