Stereoselective enol tosylation:: Preparation of trisubstituted α,β-unsaturated esters

被引：80

作者：

Baxter, JM ^{[1
]}

Steinhuebel, D ^{[1
]}

Palucki, M ^{[1
]}

Davies, IW ^{[1
]}

机构：

[1] Merck & Co Inc, Dept Proc Res, Rahway, NJ 07065 USA

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 02期

关键词：

D O I：

10.1021/ol047854z

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The stereoselective preparation of (E)- or (Z)-trisubstituted alpha,beta-unsaturated esters in three steps from N-protected glycine is presented. The key step in the synthesis is the highly selective enol tosylation of gamma-amino beta-keto esters. The enol tosylates are stable. crystalline compounds that undergo smooth and effective Suzuki-Miyaura coupling reaction with a variety of aryl boronic acids.

引用

页码：215 / 218

页数：4

共 50 条

[21] Kinetics of epoxidation of α,β-unsaturated carbonyl compounds and enol esters by dimethyldioxirane
Baumstark, AL
Chen, HH
Singh, SN
Vasquez, PC
HETEROCYCLIC COMMUNICATIONS, 2000, 6 (06) : 501 - 504
[22] Cu(i)-Catalyzed stereoselective synthesis of trisubstituted Z-enol esters via interrupting the 1,3-O-transposition reaction
Zhang, Changyuan
Chen, Lianfen
Chen, Kai
Wang, Chuntao
Xu, Zurong
Jiang, Huanfeng
Zhu, Shifa
ORGANIC CHEMISTRY FRONTIERS, 2018, 5 (16): : 2510 - 2514
[23] The intramolecular, stereoselective addition of sulfoximine carbanions to α,β-unsaturated esters
Harmata, M
Hong, XC
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (19) : 5754 - 5756
[24] ENOL ESTERS .3. PREPARATION OF DIISOPROPENYL ESTERS OF DICARBOXYLIC ACIDS
ROTHMAN, ES
SEROTA, S
SWERN, D
JOURNAL OF ORGANIC CHEMISTRY, 1966, 31 (02): : 629 - &
[25] Stereoselective synthesis of β-perfluoroalkylated α-fluoro-α,β-unsaturated esters
Jiang, Guo-Fang
Gao, Feng
Shen, Yan-Chang
Hunan Daxue Xuebao/Journal of Hunan University Natural Sciences, 2006, 33 (01): : 83 - 85
[26] Stereoselective Formation of Trisubstituted Vinyl Boronate Esters by the Acid-Mediated Elimination of α-Hydroxyboronate Esters
Guan, Weiye
Michael, Alicia K.
McIntosh, Melissa L.
Koren-Selfridge, Liza
Scott, John P.
Clark, Timothy B.
JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (15): : 7199 - 7204
[27] A STEREOSELECTIVE, 2-STEP PREPARATION OF ALPHA-ALKYL-ALPHA,BETA-UNSATURATED ESTERS
LARSON, GL
DEKAIFER, CF
SEDA, R
TORRES, LE
RAMIREZ, JR
JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (18): : 3385 - 3386
[28] Asymmetric dihydroxylation of β,γ-unsaturated carboxylic esters with trisubstituted C=C bonds -: Enantioselective syntheses of trisubstituted γ-butyrolactones
Kapferer, Tobias
Brueckner, Reinhard
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (09) : 2119 - 2133
[29] Chemo-, regio- and stereoselective preparation of silyl enol ethers from thiol esters and bis(iodozincio)alkane
Ooguri, Akihiro
Ikeda, Zenichi
Matsubara, Seijiro
CHEMICAL COMMUNICATIONS, 2007, (45) : 4761 - 4763
[30] TOSYLATION OF MONOBENZOCROWN-ESTERS AND DIBENZOCROWN-ESTERS
MARKOVSKII, LN
RUDKEVICH, DM
KALCHENKO, VI
ZHURNAL ORGANICHESKOI KHIMII, 1988, 24 (11): : 2461 - 2463

← 1 2 3 4 5 →