Enantioselective protonation of silyl enolates catalyzed by a binap-AgF complex

被引：72

作者：

Yanagisawa, A ^{[1
]}

Touge, T

Arai, T

机构：

[1] Chiba Univ, Fac Sci, Dept Chem, Inage Ku, Chiba 2638522, Japan

[2] Chiba Univ, Grad Sch Sci & Technol, Inage Ku, Chiba 2638522, Japan

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2005年 / 44卷 / 10期

关键词：

asymmetric catalysis; ketones; protonation; silver; silyl enolates;

D O I：

10.1002/anie.200462325

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Silver lining: A catalytic enantioselective protonation of trimethylsilyl enolates uses a binap/silver(I) fluoride complex as a chiral catalyst in a mixture of dichloromethane and methanol (see scheme). Various ketones with tertiary asymmetric carbon centers at the α position can be prepared with high enantioselectivities. © 2005 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：1546 / 1548

页数：3

共 40 条

[1] SYNTHESIS OF BIOLOGICAL MARKERS IN FOSSIL-FUELS .2. SYNTHESIS AND C-13 NMR-STUDIES OF SUBSTITUTED INDANS AND TETRALINS [J].

ADAMCZYK, M ;

WATT, DS ;

NETZEL, DA .

JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (22) :4226-4237

[2] Synthesis of an enantiopure 2-arylcyclohexanols from prochiral enol acetates by an enantioselective protonation/diastereoselective reduction sequence [J].

Asensio, G ;

Cuenca, A ;

Rodriguez, N ;

Medio-Simòn, M .

TETRAHEDRON-ASYMMETRY, 2003, 14 (24) :3851-3855

[3] PINACOL-TYPE REARRANGEMENTS IN PHENYLCYCLOHEXANE SERIES - EVIDENCE FOR DIFFERENCES BETWEEN REACTION MECHANISMS OF EPOXIDES AND OF CORRESPONDING DIOLS AND HALOGENOHYDRINS [J].

BERTI, G ;

MACCHIA, B ;

MACCHIA, F ;

MONTI, L .

JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1971, (20) :3371-&

[4] Enantiopure oxazolidinones as chiral acids in the asymmetric protonation of N-Boc pyrrole derived enolates [J].

Carbery, DR ;

Donohoe, TJ .

CHEMICAL COMMUNICATIONS, 2004, (06) :722-723

[5]

Dalko P. I., 2001, ANGEW CHEM-GER EDIT, V113, P3840

[6]

Dalko PI, 2001, ANGEW CHEM INT EDIT, V40, P3726, DOI 10.1002/1521-3773(20011015)40:20<3726::AID-ANIE3726>3.0.CO

[7]

2-D

[8] Recent advances into the enantioselective protonation of prostereogenic enol derivatives [J].

Eames, J ;

Weerasooriya, N .

TETRAHEDRON-ASYMMETRY, 2001, 12 (01) :1-24

[9] ENANTIOSELECTIVE DEPROTONATION OF 2 RACEMIC CYCLIC CARBONYL-COMPOUNDS BY A CHIRAL LITHIUM AMIDE [J].

ELEVELD, MB ;

HOGEVEEN, H .

TETRAHEDRON LETTERS, 1986, 27 (05) :631-634

[10]

FEHR C, 1996, ANGEW CHEM, V108, P2726

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