Asymmetric Phase-Transfer Alkylation of Readily Available Aryl Aldehyde Schiff Bases of Amino Acid Ethyl Esters

被引：6

作者：

Lu, Jinying ^{[1
,2
]}

Huang, Lei ^{[1
,2
]}

Liang, Huatai ^{[1
,2
]}

Wang, Zhe ^{[1
,2
]}

Kato, Terumasa ^{[1
,2
,3
]}

Liu, Yan ^{[1
,2
]}

Maruoka, Keiji ^{[1
,2
,3
]}

机构：

[1] Guangdong Univ Technol, Sch Chem Engn & Light Ind, Guangzhou 510006, Peoples R China

[2] Guangdong Univ Technol, Guangdong Prov Key Lab Plant Resources Biorefinery, Guangzhou 510006, Peoples R China

[3] Kyoto Univ, Grad Sch Pharmaceut Sci, Lab Organocatalyt Chem, Sakyo Ku, Kyoto 6068501, Japan

来源：

ORGANIC LETTERS | 2024年 / 26卷 / 20期

基金：

中国国家自然科学基金;

关键词：

CATALYTIC ENANTIOSELECTIVE SYNTHESIS; ALPHA-AMINO; ALPHA; ALPHA-DIALKYL-ALPHA-AMINO ACIDS; AMMONIUM-SALTS; DERIVATIVES; DISCOVERY; PEPTIDES; DESIGN; MILD;

D O I：

10.1021/acs.orglett.3c04290

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Asymmetric phase-transfer alkylation of the N-(arylmethylene)-alpha-alkylamino acid ethyl esters and N-(arylmethylene)glycine ethyl esters was found to be catalyzed by the (R)- or (S)-Simplified Maruoka Catalyst with high efficiency and excellent enantioselectivity. This approach was successfully applied to the enantioselective formal synthesis of the angiotensin II type 2 receptor (AT2R) antagonists Olodanrigan and LX9211, and the practical aspect is demonstrated by the kilogram-scale synthesis of a key intermediate for the synthesis of LX9211.

引用

页码：4163 / 4167

页数：5

共 50 条

[1] Preparation of Chiral Amino Esters by Asymmetric Phase-Transfer Catalyzed Alkylations of Schiff Bases in a Ball Mill
Nun, Pierrick
Perez, Violaine
Calmes, Monique
Martinez, Jean
Lamaty, Frederic
CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (12) : 3773 - 3779
[2] Synthesis and asymmetric phase-transfer catalytic alkylation of L-dopa Schiff bases
Cui, Jian-Guo
Zhong, Yi-Ning
Gan, Chun-Fang
Huang, Chu-Sheng
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2008, 28 (01) : 78 - 83
[3] Orthopalladated complexes as phase-transfer catalysts for asymmetric alkylation of achiral Schiff base esters
Dae Hyun Kim
Jin Kyu Im
Dae Won Kim
Hyunjoo Lee
Honggan Kim
Hoon Sik Kim
Minserk Cheong
Deb Kumar Mukherjee
Transition Metal Chemistry, 2010, 35 : 949 - 957
[4] Orthopalladated complexes as phase-transfer catalysts for asymmetric alkylation of achiral Schiff base esters
Kim, Dae Hyun
Im, Jin Kyu
Kim, Dae Won
Lee, Hyunjoo
Kim, Honggan
Kim, Hoon Sik
Cheong, Minserk
Mukherjee, Deb Kumar
TRANSITION METAL CHEMISTRY, 2010, 35 (08) : 949 - 957
[5] Asymmetric -alkylation of cyclic -keto esters and -keto amides by phase-transfer catalysis
Wang, Yakun
Li, Yueyun
Lian, Mingming
Zhang, Jixia
Liu, Zhaomin
Tang, Xiaofei
Yin, Hang
Meng, Qingwei
ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (03) : 573 - 584
[6] Enantioselective Alkylation of α-Fluoro-β-Keto Esters by Asymmetric Phase-Transfer Catalysis
Ding, Changhua
Maruoka, Keiji
SYNLETT, 2009, (04) : 664 - 666
[7] Alkylation of Pyrazoles with Ethyl Chloroacetate under Phase-Transfer Catalysis and Hydrolysis of the Esters Obtained
Rstakyan, V. I.
Hakobyan, A. E.
Zakaryan, G. B.
Hayotsyan, S. S.
Attaryan, H. S.
Asratyan, G. V.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2014, 84 (08) : 1641 - 1643
[8] Alkylation of pyrazoles with ethyl chloroacetate under phase-transfer catalysis and hydrolysis of the esters obtained
V. I. Rstakyan
A. E. Hakobyan
G. B. Zakaryan
S. S. Hayotsyan
H. S. Attaryan
G. V. Asratyan
Russian Journal of General Chemistry, 2014, 84 : 1641 - 1643
[9] Enantioselective synthesis of bis-α-amino acid esters via asymmetric phase-transfer catalysis.
Lygo, B
Crosby, J
Peterson, JA
TETRAHEDRON LETTERS, 1999, 40 (07) : 1385 - 1388
[10] The enantioselective synthesis of α-amino acids by phase-transfer catalysis with achiral Schiff base esters
O'Donnell, MJ
ACCOUNTS OF CHEMICAL RESEARCH, 2004, 37 (08) : 506 - 517

← 1 2 3 4 5 →