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Epoxy and aziridinyl enolsilanes in diastereoselective inter- and intramolecular Friedel–Crafts alkylations
Literature Information
Publication Date
2016-02-12
DOI
10.1039/C5QO00333D
Impact Factor
5.281
Authors
Sze Kui Lam, Brian Lo, Wing-Tak Wong, Jian Sun, Guanhua Chen
View Original
Abstract
The Friedel–Crafts alkylations of epoxy enolsilanes with arenes occur under silyl triflate catalysis at low temperatures. Intermolecular alkylations with optically-enriched epoxides occur with conservation of ee. Intramolecular reactions give rise to cyclized products with high diastereoselectivity in good yields. Aziridinyl enolsilanes also undergo selective inter- and intramolecular Friedel–Crafts reactions in a similar manner.
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Organic Chemistry Frontiers
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