Application of asymmetric alkylation of malonic diester with phase-transfer catalysis: synthesis of LFA-1 antagonist BIRT-377

被引：8

作者：

Kanemitsu, Takuya ^{[1
]}

Furukoshi, Saeka ^{[1
]}

Miyazaki, Michiko ^{[1
]}

Nagata, Kazuhiro ^{[1
]}

Itoh, Takashi ^{[1
]}

机构：

[1] Showa Univ, Sch Pharm, Shinagawa Ku, Tokyo 1428555, Japan

来源：

TETRAHEDRON-ASYMMETRY | 2015年 / 26卷 / 04期

基金：

日本学术振兴会;

关键词：

ALPHA-AMINO-ACIDS; ENANTIOSELECTIVE SYNTHESIS; ALPHA; ALPHA-DIALKYL-ALPHA-AMINO ACIDS; CONVENIENT PREPARATION; CONSTRUCTION; DESYMMETRIZATION; REAGENT;

D O I：

10.1016/j.tetasy.2015.01.006

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

An efficient asymmetric synthesis of LFA-1 antagonist BIRT-377 using enantioselective phase-transfer catalytic alkylation has been developed. The alkylation of alpha-monosubstituted tert-butyl methyl malonate was catalyzed by a quaternary ammonium salt derived from a cinchona alkaloid to obtain the product with a quaternary stereogenic carbon in high yield and with high enantioselectivity. The chiral alpha,alpha-disubstituted product thus obtained was transformed into BIRT-377 through alternating chemoselective deprotection of the two ester groups followed by Curtius rearrangement. (C) 2015 Elsevier Ltd. All rights reserved.

引用

页码：214 / 218

页数：5

共 19 条

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Johnson, Aaron
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ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (05) : 1463 - 1469
[2] Asymmetric Alkylation of Malonic Diester Under Phase-Transfer Conditions
Kanemitsu, Takuya
Koga, Shintaro
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Miyazaki, Michiko
Nagata, Kazuhiro
Itoh, Takashi
ACS CATALYSIS, 2011, 1 (10): : 1331 - 1335
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Han, ZF
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TETRAHEDRON LETTERS, 2005, 46 (49) : 8555 - 8558
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Wang, Yong-Gang
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JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (22) : 8651 - 8654
[6] Asymmetric -alkylation of cyclic -keto esters and -keto amides by phase-transfer catalysis
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Maruoka, Keiji
SYNLETT, 2009, (04) : 664 - 666
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White, James D.
Suttisintong, Khomson
JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (06) : 2757 - 2762
[9] Enantioselective Alkylation of N-Arylhydrazones Derived from -Keto Esters and Isatin Derivatives through Asymmetric Phase-Transfer Catalysis
Kang, Qi-Kai
Selvakumar, Sermadurai
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CHEMISTRY-AN ASIAN JOURNAL, 2018, 13 (14) : 1780 - 1783
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Huang, Li
Jin, Can
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JOURNAL OF CHEMICAL RESEARCH, 2012, (09) : 532 - 535

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