Studies on the synthesis of α-iodoaziridines and improved conditions for the synthesis of alkyl-α-iodoaziridines using ClMgCHI2

TETRAHEDRON

卷:71

Article

Boultwood, Tom¹  Affron, Dominic P.¹  Bull, James A.¹ 

[1] Univ London Imperial Coll Sci Technol & Med, Dept Chem, London SW7 2AZ, England

关键词: Aziridines;    Carbenoids;    Diiodomethyllithium;    Diiodomethylmagnesium chloride;    Cyclisation;   

DOI  :  10.1016/j.tet.2015.05.098

来源: Elsevier

【 摘 要 】

alpha-lodoaziridines are unusual motifs and intriguing structures for further functionalisation of the intact aziridine. The preparation of N-protected alpha-iodoaziridines is achieved through an addition-cyclisation reaction of LiCHl(2) with imines. The effects of varying the N-group and using different carbenoids are investigated. Excellent cis-stereochemistry is achieved, except for N-carbamates containing aryl groups. Using the mixed carbenoid LiCHICl, the iodide leaving group is selected for cyclisation affording chloroaziridines only, as a cis/trans mixture. More convenient and higher yielding conditions for the preparation of alkyl N-Ts alpha-iodoaziridines are developed, using ClMgCHI2. Additionally, the formation of the problematic primary alkyl alpha-iodoaziridines is achieved. (C) 2015 Elsevier Ltd. All rights reserved.

【 授权许可】

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