Asymmetric Synthesis of 2-(2-Pyridyl)aziridines from 2-Pyridineimines Bearing Stereogenic N-Alkyl Substituents and Regioselective Opening of the Aziridine Ring

详细信息    查看全文

• 作者：Diego Savoia ; Giuseppe Alvaro ; Romano Di Fabio ; Andrea Gualandi ; Claudio Fiorelli
• 刊名：Journal of Organic Chemistry
• 出版年：2006
• 出版时间：December 8, 2006
• 年：2006
• 卷：71
• 期：25
• 页码：9373 - 9381
• 全文大小：167K
• 年卷期：v.71,no.25(December 8, 2006)
• ISSN：1520-6904

文摘

The addition of chloromethyllithium to the imine derived from 2-pyridinecarboxaldehyde and (S)-valinol,protected as its O-trimethylsilyl ether, gave the 1,2-disubstituted aziridine with good yield anddiastereoselectivity. The analogous reaction performed on the imine derived from (S)-valine methyl estergave the product containing the aziridine ring and the -chloro ketone group coming from the attack ofchloromethyllithium to the ester function. Other stereogenic alkyl substituents at nitrogen gave lesssatisfactory results. Moreover, the aziridination protocol did not work on other aromatic imines whichwere not capable of bidentate chelation, e.g., 3- and 4-pyridineimine and benzaldimine. Preliminary studiesshowed the possibility to carry out regio- and stereospecific opening reactions of 2-(2-pyridyl)aziridinesby attack of internally generated or external nucleophiles.