Highly Diastereoselective and Enantioselective Synthesis of α-Hydroxy β-Amino Acid Derivatives: Lewis Base Catalyzed Hydrosilylation of α-Acetoxy β-Enamino Esters

被引：98

作者：

Jiang, Yan ^{[1
,2
]}

Chen, Xing ^{[1
,2
]}

Zheng, Yongsheng ^{[1
,2
]}

Xue, Zhouyang ^{[1
,2
]}

Shu, Chang ^{[1
,2
]}

Yuan, Weicheng ^{[1
]}

Zhang, Xiaomei ^{[1
]}

机构：

[1] Chinese Acad Sci, Chengdu Inst Organ Chem, Key Lab Asymmetr Synth & Chiraltechnol Sichuan Pr, Chengdu 610041, Peoples R China

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

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2011年 / 50卷 / 32期

关键词：

amino acids; asymmetric catalysis; Lewis bases; organocatalysis; synthetic methods; TAXOL SIDE-CHAIN; SHARPLESS ASYMMETRIC AMINOHYDROXYLATION; 1,3-DIPOLAR CYCLOADDITIONS; STEREOSELECTIVE-SYNTHESIS; EFFICIENT SYNTHESIS; CARBONYL YLIDES; REDUCTION; IMINES; CHEMISTRY; TAXOTERE;

D O I：

10.1002/anie.201102150

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

By design: A series of α-acetoxy-β-enamino esters 1 were synthesized and then subjected to catalytic asymmetric hydrosilylation. In the presence of a chiral Lewis base catalyst, the reactions proceeded smoothly to provide a wide range of chiral α-acetoxy β-amino acid derivatives in high yields with good diastereoselectivities and enantioselectivities. Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：7304 / 7307

页数：4

共 50 条

[1] Highly Enantioselective Synthesis of β-Amino Acid Derivatives by the Lewis Base Catalyzed Hydrosilylation of β-Enamino Esters
Zheng, Hong-Jie
Chen, Wen-Bing
Wu, Zhi-Jun
Deng, Jin-Gen
Lin, Wen-Qing
Yuan, Wei-Cheng
Zhang, Xiao-Mei
CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (32) : 9864 - 9867
[2] Highly Enantioselective Lewis Base Organocatalyzed Hydrosilylation of γ-Imino Esters
Xue, Zhou-Yang
Liu, Li-Xin
Jiang, Yan
Yuan, Wei-Cheng
Zhang, Xiao-Mei
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 2012 (02) : 251 - 255
[3] Stereoselective Lewis Base-Catalyzed Asymmetric Hydrosilylation of α-Acetamido-β-enamino Esters: Straightforward Approach for the Construction of α,β-Diamino Acid Derivatives
Jiang, Yan
Chen, Xing
Hu, Xiao-Yan
Shu, Chang
Zhang, Yong-Hong
Zheng, Yong-Sheng
Lian, Chun-Xia
Yuan, Wei-Cheng
Zhang, Xiao-Mei
ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (10) : 1931 - 1936
[4] The First Highly Enantioselective Lewis Base Organocatalyzed Hydrosilylation of α-Imino Esters
Xue, Zhou-Yang
Jiang, Yan
Yuan, Wei-Cheng
Zhang, Xiao-Mei
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (04) : 616 - 619
[5] A Highly Diastereoselective Synthesis of α-Hydroxy-β-amino Acid Derivatives via a Lewis Acid Catalyzed Three-Component Condensation Reaction
Gassa, Federico
Contini, Alessandro
Fontana, Gabriele
Pellegrino, Sara
Gelmi, Maria Luisa
JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (21): : 7099 - 7106
[6] Chiral Lewis Base Catalyzed Highly Enantioselective Reduction of N-Alkyl β-Enamino Esters with Trichlorosilane and Water
Wu, Xinjun
Li, Yang
Wang, Chao
Zhou, Li
Lu, Xiaoxia
Sun, Jian
CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (10) : 2846 - 2848
[7] Chiral Lewis Base-Catalyzed, Enantioselective Reduction of Unprotected β-Enamino Esters with Trichlorosilane
Ye, Jianheng
Wang, Chao
Chen, Lin
Wu, Xinjun
Zhou, Li
Sun, Jian
ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (07) : 1042 - 1047
[8] Highly diastereoselective Michael addition of α-hydroxy acid derivatives and enantioselective synthesis of (+)-crobarbatic acid
Jang, DP
Chang, JW
Uang, BJ
ORGANIC LETTERS, 2001, 3 (07) : 983 - 985
[9] Lewis Base Catalyzed Asymmetric Hydrosilylation of α-Substituted β-Enamino Esters: Facile Access to Enantioenriched β2-Amino Esters via Dynamic Kinetic Resolution
Shu, Chang
Hu, Xiao-Yan
Li, Shuai-Shuai
Yuan, Wei-Cheng
Zhang, Xiao-Mei
SYNLETT, 2014, 25 (13) : 1879 - 1882
[10] Synthesis of a series of novel chiral Lewis base catalysts and their application in promoting asymmetric hydrosilylation of β-enamino esters
Chen, Xing
Hu, Xiao-Yan
Shu, Chang
Zhang, Yong-Hong
Zheng, Yong-Sheng
Jiang, Yan
Yuan, Wei-Cheng
Liu, Bo
Zhang, Xiao-Mei
ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (19) : 3089 - 3093

← 1 2 3 4 5 →