Enantioselective Synthesis of Dialkylated α-Hydroxy Carboxylic Acids through Asymmetric Phase-Transfer Catalysis

被引：32

作者：

Duan, Shaobo ^{[1
]}

Li, Sanliang ^{[1
]}

Ye, Xinyi ^{[2
]}

Du, Nuan-Nuan ^{[1
]}

Tan, Choon-Hong ^{[1
,2
]}

Jiang, Zhiyong ^{[1
]}

机构：

[1] Henan Univ, Key Lab Nat Med & Immunoengn Henan Prov, Kaifeng 475004, Henan, Peoples R China

[2] Nanyang Technol Univ, Div Chem & Biol Chem, Singapore 637371, Singapore

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2015年 / 80卷 / 15期

关键词：

STEREOSELECTIVE-SYNTHESIS; MICHAEL ADDITION; MANNICH REACTIONS; GLYCOLIC ACID; 5H-OXAZOL-4-ONES; DERIVATIVES; ESTERS; HYDROLYZES; KETONES;

D O I：

10.1021/acs.joc.5b01081

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In the presence of an L-tert-leucine-derived urea ammonium salt as phase-transfer catalyst, a highly enantioselective alkylation of 5H-oxazol-4-ones with various benzyl bromides and allylic bromides has been developed to furnish catalytic asymmetric synthesis of biologically important dialkylated a-hydroxy carboxylic acids with a broad scope. This is the first example of an L-amino acid-derived urea ammonium salt being used as a phase-transfer catalyst with excellent catalytic efficiency.

引用

页码：7770 / 7778

页数：9

共 50 条

[1] Studies on the enantioselective synthesis of α-amino acids via asymmetric phase-transfer catalysis
Lygo, B
Crosby, J
Lowdon, TR
Peterson, JA
Wainwright, PG
TETRAHEDRON, 2001, 57 (12) : 2403 - 2409
[2] Enantioselective synthesis of α-amino acids by chiral phase-transfer catalysis
Ooi, T
Maruoka, K
JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2003, 61 (12) : 1195 - 1206
[3] THE ENANTIOSELECTIVE SYNTHESIS OF ALPHA-AMINO-ACIDS BY PHASE-TRANSFER CATALYSIS
ODONNELL, MJ
WU, SD
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1991, 201 : 132 - ORGN
[4] Enantioselective Phase-Transfer Catalysis: Synthesis of Pyrazolines
Mahe, Olivier
Dez, Isabelle
Levacher, Vincent
Briere, Jean-Francois
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (39) : 7072 - 7075
[5] Enantioselective synthesis of dityrosine and isodityrosine via asymmetric phase-transfer catalysis.
Lygo, B
TETRAHEDRON LETTERS, 1999, 40 (07) : 1389 - 1392
[6] 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
[7] Asymmetric phase-transfer catalysis
Lee, Hyo-Jun
Maruoka, Keiji
NATURE REVIEWS CHEMISTRY, 2024, 8 (11) : 851 - 869
[8] Asymmetric phase-transfer catalysis
Nelson, A
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1999, 38 (11) : 1583 - 1585
[9] Enantioselective amino acid synthesis by chiral phase-transfer catalysis
Maruoka, K
Ooi, T
CHEMICAL REVIEWS, 2003, 103 (08) : 3013 - 3028
[10] Practical catalytic enantioselective synthesis of α,α-dialkyl-α-amino acids by chiral phase-transfer catalysis
Ooi, T
Takeuchi, M
Kameda, M
Maruoka, K
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (21) : 5228 - 5229

← 1 2 3 4 5 →