(Z)-Selective Enol Triflation of α-Alkoxyacetoaldehydes: Application to Synthesis of (Z)-Allylic Alcohols via Cross-Coupling Reaction and [1,2-Wittig Rearrangement

被引：10

作者：

Kurosawa, Fumiya ^{[1
]}

Nakano, Takeo ^{[1
]}

Soeta, Takahiro ^{[1
]}

Endo, Kohei ^{[1
]}

Ukaji, Yutaka ^{[1
]}

机构：

[1] Kanazawa Univ, Grad Sch Nat Sci & Technol, Div Mat Chem, Kanazawa, Ishikawa 9201192, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2015年 / 80卷 / 11期

基金：

日本学术振兴会;

关键词：

GRIGNARD-REAGENTS; STEREOCONTROLLED SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; ASYMMETRIC-SYNTHESIS; BROOK REARRANGEMENT; ALLYLIC ALCOHOLS; Z-ALKENES; VINYL; 1,4-ELIMINATION; FACILE;

D O I：

10.1021/acs.joc.5b00647

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The stereoselective transformation of alpha-alkoxyacetoaldehydes to the corresponding (Z)-vinyl triflates was achieved by treatment with phenyl triflimide and DBU. The stereochemistry was explained by the "syn-effect," which was attributed primarily to an sigma -> pi* interaction. The,beta-alkoxy vinyl triflates obtained were applied to the stereoselective synthesis of structurally diverse (Z)-allylic alcohols via transition metal-catalyzed cross-coupling reaction and [1,2]-Wittig rearrangement.

引用

页码：5696 / 5703

页数：8

共 91 条

[1] Hydroxy group directivity in the epoxidation of chiral allylic alcohols: Control of diastereoselectivity through allylic strain and hydrogen bonding [J].

Adam, W ;

Wirth, T .

ACCOUNTS OF CHEMICAL RESEARCH, 1999, 32 (08) :703-710

[2] Highly enantioselective hydrogenation of aryl vinyl ketones to allylic alcohols catalyzed by the tol-binap/dmapen ruthenium(II) complex [J].

Arai, Noriyoshi ;

Azuma, Keita ;

Nii, Noriyuki ;

Ohkuma, Takeshi .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (39) :7457-7460

[3] Stereoselective synthesis of acetoacetate-derived enol triflates [J].

Babinski, David ;

Soltani, Omid ;

Frantz, Doug E. .

ORGANIC LETTERS, 2008, 10 (13) :2901-2904

[4]

Banert K, 2000, EUR J ORG CHEM, V2000, P257

[5] Chemical transformations induced by triflic anhydride [J].

Baraznenok, IL ;

Nenajdenko, VG ;

Balenkova, ES .

TETRAHEDRON, 2000, 56 (20) :3077-3119

[6] Tris(trimethylsilyl)silyl-governed aldehyde cross-aldol cascade reaction [J].

Boxer, MB ;

Yamamoto, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (01) :48-49

[7] Ru-based Z-selective metathesis catalysts with modified cyclometalated carbene ligands [J].

Bronner, Sarah M. ;

Herbert, Myles B. ;

Patel, Paresma R. ;

Marx, Vanessa M. ;

Grubbs, Robert H. .

CHEMICAL SCIENCE, 2014, 5 (10) :4091-4098

[8] Cross coupling of vinyl triflates and alkyl Grignard reagents catalyzed by Nickel(0)-complexes [J].

Busacca, CA ;

Eriksson, MC ;

Fiaschi, R .

TETRAHEDRON LETTERS, 1999, 40 (16) :3101-3104

[9] New palladium-catalyzed reactions of unsaturated triflates with alkenes and alkynes [J].

Cacchi, S .

PURE AND APPLIED CHEMISTRY, 1996, 68 (01) :45-52

[10] Vinyl triflates derived from 1,3-dicarbonyl compounds and analogs: access and applications to organic synthesis [J].

Chassaing, Stefan ;

Specklin, Simon ;

Weibel, Jean-Marc ;

Pale, Patrick .

TETRAHEDRON, 2012, 68 (36) :7245-7273

← 1 2 3 4 5 6 7 8 9 10 →