Epoxy and aziridinyl enolsilanes in diastereoselective inter- and intramolecular Friedel-Crafts alkylations

Jesse Ling, Sze Kui Lam, Brian Lo, Sarah Lam, Wing Tak Wong, Jian Sun, Guanhua Chen, Pauline Chiu

Research output: Journal article publicationJournal articleAcademic researchpeer-review

17 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)457-461
Number of pages5
JournalOrganic Chemistry Frontiers
Volume3
Issue number4
DOIs
Publication statusPublished - Apr 2016

ASJC Scopus subject areas

  • Organic Chemistry

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