Cu(I)-catalyzed sulfoximination

被引：52

作者：

Müller, JFK ^{[1
]}

Vogt, P ^{[1
]}

机构：

[1] Univ Basel, Inst Inorgan Chem, CH-4056 Basel, Switzerland

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 27期

关键词：

catalysis; copper; sulfoximines;

D O I：

10.1016/S0040-4039(98)00925-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of PhI=NTs with sulfoxides in the presence of catalytic amounts of CuOTf afforded the corresponding N-tosylsulfoximines in high yield. The use of enantiomerically pure sulfoxides allowed stereoselective access to N-tosylsulfoximines with complete retention of configuration at sulfur. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：4805 / 4806

页数：2

共 12 条

[1] An efficient resolution of (+/-)-S-methyl-S-phenylsulfoximine with (+)-10-camphorsulfonic acid by the method of half-quantities [J].

Brandt, J ;

Gais, HJ .

TETRAHEDRON-ASYMMETRY, 1997, 8 (06) :909-912

[2] STEREOCHEMISTRY OF SULFUR COMPOUNDS .1. STEREOCHEMICAL REACTION CYCLES INVOLVING AN OPEN CHAIN SULFOXIDE, SULFIMIDE, AND SULFOXIMIDE [J].

CRAM, DJ ;

DAY, J ;

RAYNER, DR ;

SCHRILTZ, DM ;

DUCHAMP, DJ ;

GARWOOD, DC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1970, 92 (25) :7369-&

[3] REGIOSELECTIVE AND ENANTIOSELECTIVE SUBSTITUTION OF PRIMARY ENDOCYCLIC ALLYLIC SULFOXIMINES WITH ORGANOCOPPER AND ORGANOCUPRATE REAGENTS - THE IMPORTANCE OF IODIDE FOR THE ALLYLIC SUBSTITUTION WITH ORGANOCOPPER COMPOUNDS [J].

GAIS, HJ ;

MULLER, H ;

BUND, J ;

SCOMMODA, M ;

BRANDT, J ;

RAABE, G .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (09) :2453-2466

[4] SYNTHESIS OF OPTICALLY-ACTIVE SULFOXIMINES FROM OPTICALLY-ACTIVE SULFOXIDES [J].

JOHNSON, CR ;

KIRCHHOF.RA ;

CORKINS, HG .

JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (16) :2458-2459

[5] PREPARATION AND REACTIONS OF SULFONIMIDOYL FLUORIDES [J].

JOHNSON, CR ;

BIS, KG ;

CANTILLO, JH ;

MEANWELL, NA ;

REINHARD, MFD ;

ZELLER, JR ;

VONK, GP .

JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (01) :1-3

[6] ASYMMETRIC ALKENE AZIRIDINATION WITH READILY AVAILABLE CHIRAL DIIMINE-BASED CATALYSTS [J].

LI, Z ;

CONSER, KR ;

JACOBSEN, EN .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (12) :5326-5327

[7] Structure and reactivity of a sulfoximine-stabilized chiral dilithiocarbanion [J].

Muller, JFK ;

Neuburger, M ;

Zehnder, M .

HELVETICA CHIMICA ACTA, 1997, 80 (07) :2182-2190

[8] ASYMMETRIC CONJUGATE ADDITION OF ORGANOMETALLIC REAGENTS TO CHIRAL VINYL SULFOXIMINES [J].

PYNE, SG .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (01) :81-87

[9] A GENERAL-ROUTE TO ENANTIOMERICALLY PURE SULFOXIDES FROM A CHIRAL SULFITE [J].

REBIERE, F ;

SAMUEL, O ;

RICARD, L ;

KAGAN, HB .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (21) :5991-5999

[10] Metalated 2-alkenylsulfoximines: Efficient solutions for asymmetric d(3)-synthons [J].

Reggelin, M ;

Weinberger, H ;

Gerlach, M ;

Welcker, R .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (20) :4765-4777

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