STEREOSELECTIVE PROTONATION AND REDUCTION OF BETA-SULFINYL ENAMINES - X-RAY MOLECULAR-STRUCTURE OF N-BENZYL-2-(PARA-TOLYSULPHINYL)PROPYLAMINE

被引：7

作者：

KAWECKI, R

KOZERSKI, L

URBANCZYKLIPKOWSKA, Z

BOCELLI, G

机构：

[1] POLISH ACAD SCI,INST ORGAN CHEM,KASPRZAKA 44,PL-01224 WARSAW,POLAND

[2] CNR,CTR STUDIO STRUTTURIST DIFFRATTOMETR,I-43100 PARMA,ITALY

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1991年 / 09期

关键词：

D O I：

10.1039/p19910002255

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reduction of beta-substituted beta-sulphinyl enamines by acyloxyborohydrides in the presence of carboxylic acids leads to beta-sulphinyl amines in good chemical yield and diastereoisomeric excess (de) up to 92%. Two methods of reduction, differing by the introduction sequence of the acid, are examined. The stereoselectivity is enhanced with large proton donors and strong acids but is less dependent on the type of reducing agent and solvent used. A mechanism for the stereoselective protonation is proposed.

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页码：2255 / 2260

页数：6

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