Z- and E-selective Horner-Wadsworth-Emmons reactions

被引：6

作者：

Molnar, Katalin ^{[1
]}

Takacs, Laszlo ^{[1
]}

Kadar, Mihaly ^{[1
]}

Faigl, Ferenc ^{[2
]}

Kardos, Zsuzsanna ^{[1
]}

机构：

[1] Sanofi, Prostaglandin Business Unit, To St 1-5, H-1045 Budapest, Hungary

[2] Budapest Univ Technol & Econ, Hungarian Acad Sci, MTA BME Organ Chem Technol Res Grp, Budapest, Hungary

来源：

SYNTHETIC COMMUNICATIONS | 2017年 / 47卷 / 13期

关键词：

Bis(trifluoroethyl) phosphonates; Horner-Wadsworth-Emmons reaction; stereoselectivity; -unsaturated ketones; Z-UNSATURATED ESTERS; ETHYL (DIARYLPHOSPHONO)ACETATES; OLEFINATION; STEREOCHEMISTRY; CARBANIONS;

D O I：

10.1080/00397911.2017.1319487

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In the present work, we determined and evaluated the stereochemical outcome of the Horner-Wadsworth-Emmons (HWE) reaction of 2-oxoalkylphosphonates with different ester functions (bis(2,2,2-trifluoroethyl), 2,2,2-trifluoroethyl methyl, dimethyl) and side chains (aliphatic, aromatic) with three different aldehydes (benzaldehyde, THP- and PPB-protected Corey aldehydes) under two reaction conditions. The trans protocol is generally used in the E-selective HWE reactions, while cis protocol promotes the Z-selectivity. [GRAPHICS] .

引用

页码：1214 / 1224

页数：11

共 25 条

[1] Z-selective Horner-Wadsworth-Emmons reaction of ethyl (diarylphosphono)acetates using sodium iodide and DBU [J].

Ando, K ;

Oishi, T ;

Hirama, M ;

Ohno, H ;

Ibuka, T .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (15) :4745-4749

[2] A mechanistic study of the Horner-Wadsworth-Emmons reaction: Computational investigation on the reaction pass and the stereochemistry in the reaction of lithium enolate derived from trimethyl phosphonoacetate with acetaldehyde [J].

Ando, K .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (18) :6815-6821

[3] Z-selective Horner-Wadsworth-Emmons reaction of α-substituted ethyl (diarylphosphono)acetates with aldehydes [J].

Ando, K .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (23) :8411-8416

[4] Highly selective synthesis of Z-unsaturated esters by using new Horner-Emmons reagents, ethyl (diarylphosphono)acetates [J].

Ando, K .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (07) :1934-1939

[5] Highly Z-selective synthesis of α,β-unsaturated nitriles using the Horner-Wadsworth-Emmons reaction [J].

Ando, Kaori ;

Okumura, Miho ;

Nagaya, Shigeo .

TETRAHEDRON LETTERS, 2013, 54 (15) :2026-2028

[6]

Aswatha-Narayanappa C., 2011, PCT Int. Appl., Patent No. [WO2011055377A1, 2011055377]

[7] A quantum chemical exploration of the Horner-Wadsworth-Emmons reaction [J].

Brandt, P ;

Norrby, PO ;

Martin, I ;

Rein, T .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (04) :1280-1289

[8]

Bruckner R, 2010, ORGANIC MECHANISMS: REACTIONS, STEREOCHEMISTRY AND SYNTHESIS, P457, DOI 10.1007/978-3-642-03651-4_11

[9]

Florence G., 2004, WO Patent, Patent No. [WO 2004009574A1, 2004009574, WO 2004009574]

[10]

Granier T., 2009, PCT Int. Appl, Patent No. [WO 2009009916, 2009009916]

← 1 2 3 →