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Issue 4, 2016
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Epoxy and aziridinyl enolsilanes in diastereoselective inter- and intramolecular Friedel–Crafts alkylations

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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

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Article information


Submitted
29 Oct 2015
Accepted
12 Feb 2016
First published
12 Feb 2016

Org. Chem. Front., 2016,3, 457-461
Article type
Research Article
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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