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N-Heterocyclic carbene mediated organocatalytic transfer of tin onto aldehydes: An easy access to syn-diols and mechanistic studies

Romain Blanc 1 Paola Nava 2 Michel Rajzman 1 Laurent Commeiras 1 Jean-Luc Parrain 1, * 
* Corresponding author
1 STeRéO
ISM2 - Institut des Sciences Moléculaires de Marseille
2 CTOM - Chimie Theorique et Modèles
ISM2 - Institut des Sciences Moléculaires de Marseille
Abstract : An update of our preliminary communication concerning an efficient organocatalytic procedure for the transfer of tin onto aldehydes was proposed. This update combines 1- a full study of the preparation of γ-silyloxyallylstannanes from β-substituted enals; 2- a "one-pot" sequence (in inter- and intramolecular version) including NHC-catalyzed silylstannation reaction / Lewis Acid promoted allylstannation reaction to furnish the corresponding syn-diols; 3- mechanistic studies of the organocatalytic 1,2-addition
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https://hal.archives-ouvertes.fr/hal-00736643
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Submitted on : Friday, September 28, 2012 - 4:55:24 PM
Last modification on : Tuesday, December 14, 2021 - 4:45:47 PM

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Romain Blanc, Paola Nava, Michel Rajzman, Laurent Commeiras, Jean-Luc Parrain. N-Heterocyclic carbene mediated organocatalytic transfer of tin onto aldehydes: An easy access to syn-diols and mechanistic studies. Advanced Synthesis and Catalysis, Wiley-VCH Verlag, 2012, 354, pp.2049-2056. ⟨10.1002/adsc.201200063⟩. ⟨hal-00736643⟩

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