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

✍ Scribed by Hiroaki Ohno; Ayako Toda; Nobutaka Fujii; Yoshihisa Miwa; Tooru Taga; Yumiko Yamaoka; Eriko Osawa; Toshiro Ibuka

Publisher: Elsevier Science
Year: 1999
Tongue: French
Weight: 287 KB
Volume: 40
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(98)02604-5

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✦ Synopsis

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-alkylazJridines, exposure of the methyl carbonates of N-protected 2-alkyl-4-amino-(E)-2-alken-l-ols to Pd(PPh3) 4 (5-20 mol%) in THF or 1,4-dioxane affords predominantly the corresponding 2,3-c/s-2-alkenyl-3-alkylaziridines. These reactions can be used to synthesize either of two diastereomers from single common intermediates.

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