NDLI: Diastereo- and Regioselective Addition of Thioamide Dianions to Imines and Aziridines: Synthesis of N-Thioacyl-1,2-diamines and N-Thioacyl-1,3-diamines

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Diastereo- and Regioselective Addition of Thioamide Dianions to Imines and Aziridines: Synthesis of N-Thioacyl-1,2-diamines and N-Thioacyl-1,3-diamines

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Diastereo- and Regioselective Addition of Thioamide Dianions to Imines and Aziridines: Synthesis of N-Thioacyl-1,2-diamines and N-Thioacyl-1,3-diamines

Content Provider	World Health Organization (WHO)-Global Index Medicus
Author	Maruyama, Toshifumi Shibahara, Fumitoshi Murai, Toshiaki Kobayashi, Shun-ichiro
Description	Author Affiliation: Shibahara F ( Department of Chemistry, Faculty of Engineering, Gifu University, Yanagido, Gifu 501-1193, Japan. fshiba@gifu-u.ac.jp)
Abstract	Addition reactions of thioamide dianions that were derived from N-arylmethyl thioamides to imines and aziridines were carried out. The reactions of imines gave the addition products of N-thioacyl-1,2-diamines in a highly diastereoselective manner in good-to-excellent yields. The diastereomeric purity of these N-thioacyl-1,2-diamines could be enriched by simple recrystallization. The reduction of N-thioacyl-1,2-diamines with $LiAlH_{4}$ gave their corresponding 1,2-diamines in moderate-to-good yields with retention of their stereochemistry. The oxidative-desulfurization/cyclization of an N-thioacyl-1,2-diamine in $CuCl_{2}/O_{2}$ and $I_{2}/pyridine$ systems gave the cyclized product in moderate yield and the trans isomer was obtained as the sole product. On the other hand, a similar cyclization reaction with antiformin (aq. NaClO) as an oxidant gave the cis isomer as the major product. The reactions of N-tosylaziridines gave the addition products of N-thioacyl-1,3-diamines with low diastereoselectivity but high regioselectivity and in good-to-excellent yields. The use of $AlMe_{3}$ as an additive improved the efficiency and regioselectivity of the reaction. The stereochemistry of the obtained products was determined by X-ray diffraction.
ISSN	09476539
e-ISSN	15213765
Journal	Chemistry - A European Journal
Issue Number	1
Volume Number	19
Language	English
Publisher	Wiley-VCH;ChemPubSoc Europe
Publisher Date	2013-01-02
Publisher Place	Germany
Access Restriction	Open
Subject Keyword	Amides Chemistry Aziridines Diamines Chemical Synthesis Imines Sulfhydryl Compounds Anions Stereoisomerism Research Support, Non-U.S. Gov't
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Catalysis

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