Issue 4, 2016

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

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.

Graphical abstract: Epoxy and aziridinyl enolsilanes in diastereoselective inter- and intramolecular Friedel–Crafts alkylations

Supplementary files

Article information

Article type
Research Article
Submitted
29 Onk 2015
Accepted
12 Gur 2016
First published
12 Gur 2016

Org. Chem. Front., 2016,3, 457-461

Author version available

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

J. Ling, S. K. Lam, B. Lo, S. Lam, W. Wong, J. Sun, G. Chen and P. Chiu, Org. Chem. Front., 2016, 3, 457 DOI: 10.1039/C5QO00333D

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