Issue 14, 2014

Intermolecular (4+3) cycloadditions of aziridinyl enolsilanes

Abstract

Upon activation by strong Brønsted acids, aziridinyl enolsilanes undergo (4+3) cycloadditions with dienes to afford aminoalkylated cycloheptenones as products. The use of a highly polar medium such as nitroalkane facilitates high cycloaddition yields of up to 99%. Optically pure aziridinyl enolsilanes react to yield (4+3) cycloadducts with up to 99% ee.

Graphical abstract: Intermolecular (4+3) cycloadditions of aziridinyl enolsilanes

Supplementary files

Article information

Article type
Communication
Submitted
29 Oct 2013
Accepted
13 Dec 2013
First published
16 Dec 2013

Chem. Commun., 2014,50, 1738-1741

Intermolecular (4+3) cycloadditions of aziridinyl enolsilanes

S. K. Lam, S. Lam, W. Wong and P. Chiu, Chem. Commun., 2014, 50, 1738 DOI: 10.1039/C3CC48266A

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