Asymmetric intramolecular radical vinylation using enantiopure sulfoxides as temporary chiral auxiliaries

被引：63

作者：

Delouvrié, B ^{[1
]}

Fensterbank, L ^{[1
]}

Lacôte, E ^{[1
]}

Malacria, M ^{[1
]}

机构：

[1] Univ Paris 06, Lab Chim Organ Synth, CNRS, F-75252 Paris 05, France

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1999年 / 121卷 / 49期

关键词：

D O I：

10.1021/ja992818u

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A very diastereoselective addition-elimination sequence affords cyclopentane derivatives in high enantiomeric purities. The enantiopure sulfoxide unit serves as a very efficient temporary chiral auxiliary in this tandem reaction. Interestingly, the presence of the MAD Lewis acid totally reverses the stereochemical outcome of this reaction. Several determining parameters of this sequence have been investigated: the substitution of the vinyl sulfoxide moiety, the nature of the prochiral radical, the aromatic substituent of the sulfoxide group, the tether, and the role played by different Lewis acids.

引用

页码：11395 / 11401

页数：7

共 49 条

[1] Radical cyclisation onto imidazoles and benzimidazoles [J].

Aldabbagh, F ;

Bowman, WR .

TETRAHEDRON LETTERS, 1997, 38 (21) :3793-3794

[2] CHIRAL DIAMINES FOR A NEW PROTOCOL TO DETERMINE THE ENANTIOMERIC COMPOSITION OF ALCOHOLS, THIOLS, AND AMINES BY P-31, H-1, C-13, AND F-19 NMR [J].

ALEXAKIS, A ;

FRUTOS, JC ;

MUTTI, S ;

MANGENEY, P .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (12) :3326-3334

[3] AN EASY SYNTHESIS OF CHIRAL SULFINYL ALLYLIC BROMIDES AND THEIR USE IN THE PREPARATION OF (R)S-2-P-TOLYLSULFINYL-1,3-ALKADIENES AND (S)S-2-P-TOLYLSULFINYL-1,3-ALKADIENES [J].

BONFAND, E ;

GOSSELIN, P ;

MAIGNAN, C .

TETRAHEDRON-ASYMMETRY, 1993, 4 (07) :1667-1676

[4] STEREOCHEMISTRY OF FREE-RADICAL ELIMINATIONS ON BETA-PHENYLSULFINYL RADICALS [J].

BOOTHE, TE ;

GREENE, JL ;

SHEVLIN, PB ;

WILLCOTT, MR ;

INNERS, RR ;

CORNELIS, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (12) :3874-3879

[5]

Chatgilialoglu C., 1988, CHEM SULFONES SULFOX, P1081

[6] Synthesis of styryl tetrahydrofurans and tetrahydropyrans via addition of radicals to unsaturated sulfimides. [J].

Clark, AJ ;

Rooke, S ;

Sparey, TJ ;

Taylor, PC .

TETRAHEDRON LETTERS, 1996, 37 (06) :909-912

[7] ADDITIVE PUMMERER REACTIONS OF VINYLIC SULFOXIDES - SYNTHESIS OF GAMMA-HYDROXY-ALPHA,BETA-UNSATURATED ESTERS, ALPHA-HYDROXYKETONES, AND 2-PHENYLSULFENYL ALDEHYDES AND PRIMARY ALCOHOLS [J].

CRAIG, D ;

DANIELS, K ;

MACKENZIE, AR .

TETRAHEDRON, 1993, 49 (48) :11263-11304

[8]

Curran D. P., 1996, STEREOCHEMISTRY RADI

[9]

DJERASSI C, 1966, B SOC CHIM FR, P2378

[10] FACTORS INFLUENCING THE NATURE OF SELENIRANIUM IONS IN SELENENYL CHLORIDE ADDITIONS TO ALKENES - THE USE OF METHANOL AS SOLVENT [J].

GARRATT, DG ;

KABO, A .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1980, 58 (10) :1030-1041

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