Iron(II)-mediated nitrene transfer from t-butyloxycarbonyl azide (BocN3) to sulfoxides, sulfides, and ketene acetals

被引：81

作者：

Bach, T ^{[1
]}

Körber, C ^{[1
]}

机构：

[1] Univ Marburg, Fachbereich Chem, D-35032 Marburg, Germany

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 28期

关键词：

sulfoximides; sulfimides; catalysis; nitrenes;

D O I：

10.1016/S0040-4039(98)00927-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The nitrene transfer from t-butyloxycarbonyl azide (BocN(3)) to several nucleophiles is promoted by ferrous chloride (FeCl2) and yields the corresponding N-Boc protected sulfoximides, sulfimides, or a-amino alkanoates. Whereas the sulfoximide formation occurs spontaneously in CH2Cl2 as solvent the FeCl2-catalyzed nitrene transfer to sulfides and ketene acetals requires addition of a polar solvent. DMF was found to be best suited for this purpose. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：5015 / 5016

页数：2

共 5 条

[1] FUNCTIONALIZATION OF SATURATED-HYDROCARBONS .1. SOME REACTIONS OF A FERROUS CHLORIDE CHLORAMINE-T COMPLEX WITH HYDROCARBONS [J].

BARTON, DHR ;

HAYMOTHERWELL, RS ;

MOTHERWELL, WB .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1983, (02) :445-451

[2]

CARPINO LA, 1973, ORG SYNTH, V5, P157

[3] REACTION OF ETHYL AZIDOFORMATE WITH KETENE SILYL ACETALS [J].

CIPOLLONE, A ;

LORETO, MA ;

PELLACANI, L ;

TARDELLA, PA .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (12) :2584-2586

[4] Nitridomanganese(V) complexes: Design, preparation, and use as nitrogen atom-transfer reagents [J].

DuBois, J ;

Tomooka, CS ;

Hong, J ;

Carreira, EM .

ACCOUNTS OF CHEMICAL RESEARCH, 1997, 30 (09) :364-372

[5] UBER LICHTREAKTIONEN .13. UBER PHOTOLYTISCH UND THERMISCH ERZEUGTE ARYLSULFONYLIMENE - NACHWEIS DES BENZOYLIMENS ALS PRIMARES ZERFALLSPRODUKT DES BENZAZIDS [J].

HORNER, L ;

CHRISTMA.A .

CHEMISCHE BERICHTE-RECUEIL, 1963, 96 (02) :388-&

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