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Issue 71, 2017
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Unusual reactivity of rhodium carbenes with allenes: an efficient asymmetric synthesis of methylenetetrahydropyran scaffolds

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Abstract

A RhI/(S)-BINAP catalytic system is able to promote carbene alkyne metathesis and cascade this elemental step with an stereoselective reaction with allenes. An unusual carbene/allene reactivity is discovered that, through a formal addition of p-toluenesulfinic acid to a Rh-bound trimethylenemethane intermediate, affords 4-methylenetetrahydropyran compounds in good yields and excellent enantioselectivities.

Graphical abstract: Unusual reactivity of rhodium carbenes with allenes: an efficient asymmetric synthesis of methylenetetrahydropyran scaffolds

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Supplementary files

Article information


Submitted
20 Jun 2017
Accepted
15 Aug 2017
First published
15 Aug 2017

This article is Open Access

Chem. Commun., 2017,53, 9922-9925
Article type
Communication

Unusual reactivity of rhodium carbenes with allenes: an efficient asymmetric synthesis of methylenetetrahydropyran scaffolds

Ò. Torres, M. Solà, A. Roglans and A. Pla-Quintana, Chem. Commun., 2017, 53, 9922
DOI: 10.1039/C7CC04803C

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