Epoxy and aziridinyl enolsilanes in diastereoselective inter- and intramolecular Friedel–Crafts alkylations. Issue 4 (19th February 2016)

• Record Type: Journal Article
• Authors: Ling, Jesse; Lam, Sze Kui; Lo, Brian; Lam, Sarah; Wong, Wing-Tak; Sun, Jian; Chen, Guanhua; Chiu, Pauline
• Is Part Of: Organic chemistry frontiers. Volume 3:Issue 4(2016:Apr.)
• Page Start: 457
• Page End: 461
• Publication Date: 2016-02-19
• Subjects: Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1039/c5qo00333d
• Languages: English
• ISSNs: 2052-4110

Abstract

Abstract : Diastereoselective Friedel–Crafts reactions of optically pure epoxy enolsilanes afford enantiomerically-enriched β-hydroxy-α-arylketones. Aziridinyl enolsilanes react in an analogous manner. 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.