Issue 3, 2015

Gold(i)-catalyzed asymmetric [3 + 2]-cycloadditions of γ-1-ethoxyethoxy-propiolates and aldehydes

Abstract

A gold-catalyzed asymmetric intermolecular [3 + 2]-cycloaddition of γ-1-ethoxyethoxy-propiolate and aldehydes by the use of the chiral phosphoramidite (S,R,R)-5a is developed, which provides facile access to highly substituted 2,5-dihydrofurans in up to 84% yield with up to 97% ee. Control experiments support the result that this transformation indeed proceeds via an all-carbon gold 1,3-dipole with an open carbocation rather than a SN2 type reaction.

Graphical abstract: Gold(i)-catalyzed asymmetric [3 + 2]-cycloadditions of γ-1-ethoxyethoxy-propiolates and aldehydes

Supplementary files

Article information

Article type
Research Article
Submitted
05 10 2014
Accepted
13 1 2015
First published
14 1 2015

Org. Chem. Front., 2015,2, 221-225

Author version available

Gold(I)-catalyzed asymmetric [3 + 2]-cycloadditions of γ-1-ethoxyethoxy-propiolates and aldehydes

F. Liu, Y. Wang, W. Ye and J. Zhang, Org. Chem. Front., 2015, 2, 221 DOI: 10.1039/C4QO00261J

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