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Preparation of cysteinol derivatives by highly regioselective ring opening of nonactivated chiral aziridines by thiols

✍ Scribed by Jae Hyun Bae; Seong-Ho Shin; Chan Sun Park; Won Koo Lee

Publisher: Elsevier Science
Year: 1999
Tongue: French
Weight: 358 KB
Volume: 55
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(99)00538-4

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✦ Synopsis

Various enantiomerically pure aziridine-2-methanol derivatives 3a-I were reacted with thiophenol in methylene chloride at room temperature to obtain ring-opening products 4a-I in high yields with excellent regioselectivity. The reaction procedure is very simple and it provides highly functionalized chiral molecules potentially useful for the synthesis of many biologically important compounds. The reaction rate was found to increase with the acidity ofthiols.

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