Sterically congested chiral activated aziridines: Synthesis of both 2,3- cis- and 2,3- trans-2-alkenyl-3-alkylaziridines from common intermediates

Whereas treatment of the allylic mesylates of N-protected 2-alkyl-4-amino-( E)-2-alken-1-ols with sodium hydride in DMF yields exclusively the corresponding 2,3- trans-2-alkenyl-3-alkylaziridines, exposure of the methyl carbonates of N-protected 2-alkyl-4-amino-( E)-2-alken-1-ols to Pd(PPh 3) 4 (5–2...

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Bibliographic Details
Published in:Tetrahedron letters 1999-02, Vol.40 (7), p.1331-1334
Main Authors: Ohno, Hiroaki, Toda, Ayako, Fujii, Nobutaka, Miwa, Yoshihisa, Taga, Tooru, Yamaoka, Yumiko, Osawa, Eriko, Ibuka, Toshiro
Format: Article
Language:English
Subjects:
Aziridines
Conformation
Palladium and compounds
Stereocontrol
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Summary:Whereas treatment of the allylic mesylates of N-protected 2-alkyl-4-amino-( E)-2-alken-1-ols with sodium hydride in DMF yields exclusively the corresponding 2,3- trans-2-alkenyl-3-alkylaziridines, exposure of the methyl carbonates of N-protected 2-alkyl-4-amino-( E)-2-alken-1-ols to Pd(PPh 3) 4 (5–20 mol%) in THF or 1,4-dioxane affords predominantly the corresponding 2,3- cis-2-alkenyl-3-alkylaziridines. These reactions can be used to synthesize either of two diastereomers from single common intermediates. Graphic
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(98)02604-5