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

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

We are grateful for the financial support by the Spanish Ministry of Economy and Competitiveness (MINECO) (Project CTQ2014-54306-P) and the Generalitat de Catalunya (Project 2014-SGR-931, Xarxa de Referència en Química Teòrica i Computacional, ICREA Academia 2014 prize for M. S., and FI predoctoral grant to O.T.). The EU under the FEDER grant UNGI10-4E-801 has also funded this research

Royal Society of Chemistry (RSC)

Manager: Ministerio de Economía y Competitividad (Espanya)
Author: Torres Antón, Òscar
Solà i Puig, Miquel
Roglans i Ribas, Anna
Pla i Quintana, Anna
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
We are grateful for the financial support by the Spanish Ministry of Economy and Competitiveness (MINECO) (Project CTQ2014-54306-P) and the Generalitat de Catalunya (Project 2014-SGR-931, Xarxa de Referència en Química Teòrica i Computacional, ICREA Academia 2014 prize for M. S., and FI predoctoral grant to O.T.). The EU under the FEDER grant UNGI10-4E-801 has also funded this research
Document access: http://hdl.handle.net/2072/299833
Language: eng
Publisher: Royal Society of Chemistry (RSC)
Rights: Attribution-NonCommercial 3.0 Spain
Rights URI: http://creativecommons.org/licenses/by-nc/3.0/es/
Subject: Síntesi asimètrica
Asymmetric synthesis
Catalitzadors de rodi
Rhodium catalyst
Al·lens
Allenes
Title: Unusual reactivity of rhodium carbenes with allenes: an efficient asymmetric synthesis of methylenetetrahydropyran scaffolds
Type: info:eu-repo/semantics/article
Repository: Recercat

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