A facile synthesis of N-sulfinylaldimines

被引：16

作者：

Ardej-Jakubisiak, Monika ^{[1
]}

Kawecki, Robert ^{[1
,2
]}

Swietlinska, Aneta ^{[1
]}

机构：

[1] Univ Podlasie, Inst Chem, PL-08110 Siedlce, Poland

[2] Polish Acad Sci, Inst Organ Chem, PL-01224 Warsaw, Poland

来源：

TETRAHEDRON-ASYMMETRY | 2007年 / 18卷 / 21期

关键词：

D O I：

10.1016/j.tetasy.2007.10.015

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A simple and efficient procedure for the synthesis of N-sulfinylaldimines (sulfinimines) from sulfinamides and aldehydes is described. The reaction was carried out in the presence of t-BuOK or NaOH. The method is applicable for the synthesis of optically active sulfinimines. (c) 2007 Elsevier Ltd. All rights reserved.

引用

页码：2507 / 2509

页数：3

共 15 条

[1] ASYMMETRIC INDUCTION IN THE REDUCTION OF OPTICALLY-ACTIVE N-ALKYLIDENESULFINAMIDES BY METAL-HYDRIDES - A NEW, EFFICIENT ENANTIOSELECTIVE ROUTE TO CHIRAL AMINES [J].

ANNUNZIATA, R ;

CINQUINI, M ;

COZZI, F .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1982, (02) :339-343

[2] ASYMMETRIC-SYNTHESIS OF SULFINIMINES - APPLICATIONS TO THE SYNTHESIS OF NONRACEMIC BETA-AMINO-ACIDS AND ALPHA-HYDROXYL-BETA-AMINO-ACIDS [J].

DAVIS, FA ;

REDDY, RT ;

REDDY, RE .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (24) :6387-6389

[3] Asymmetric synthesis using suffinimines (N-sulfinyl imines) [J].

Davis, FA ;

Yang, B ;

Deng, JH ;

Wu, YZ ;

Zhang, Y ;

Rao, A ;

Fang, TN ;

Goswami, R ;

Prasad, KR ;

Nolt, MB ;

Anilkumar, G .

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2005, 180 (5-6) :1109-1117

[4] Asymmetric synthesis and properties of sulfinimines (thiooxime S-oxides) [J].

Davis, FA ;

Reddy, RE ;

Szewczyk, JM ;

Reddy, GV ;

Portonovo, PS ;

Zhang, HM ;

Fanelli, D ;

Reddy, RT ;

Zhou, P ;

Carroll, PJ .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (08) :2555-2563

[5] Improved synthesis of enantiopure sulfinimines (thiooxime S-oxides) from p-toluenesulfinamide and aldehydes and ketones [J].

Davis, FA ;

Zhang, YL ;

Andemichael, Y ;

Fang, TA ;

Fanelli, DL ;

Zhang, HM .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (04) :1403-1406

[6] ASYMMETRIC-SYNTHESIS OF SULFINIMINES - CHIRAL AMMONIA IMINE SYNTHONS [J].

DAVIS, FA ;

REDDY, RE ;

SZEWCZYK, JM ;

PORTONOVO, PS .

TETRAHEDRON LETTERS, 1993, 34 (39) :6229-6232

[7] N-tert-Butanesulfinyl imines:: Versatile intermediates for the asymmetric synthesis of amines [J].

Ellman, JA ;

Owens, TD ;

Tang, TP .

ACCOUNTS OF CHEMICAL RESEARCH, 2002, 35 (11) :984-995

[8] Synthesis of sulfinimines by direct condensation of sulfinamides with aldehydes using Cs2CO3 as an activating and dehydrating reagent [J].

Higashibayashi, S ;

Tohmiya, H ;

Mori, T ;

Hashimoto, K ;

Nakata, M .

SYNLETT, 2004, (03) :457-460

[9] KHSO4-mediated condensation reactions of tert-butanesulfinamide with aldehydes.: Preparation of tert-butanesulfinyl aldimines [J].

Huang, ZY ;

Zhang, M ;

Wang, Y ;

Qin, Y .

SYNLETT, 2005, (08) :1334-1336

[10] Synthesis of enantiopure sulfinimines (thiooxime S-oxides) catalyzed by Yb(OTf)3 from p-toluenesulfinamide and aldehydes in mild reaction conditions [J].

Jiang, ZY ;

Chan, WH ;

Lee, AWM .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (03) :1081-1083

← 1 2 →