Rhodium-Catalyzed Methylenation of Aldehydes
Hélène Lebel* and Valérie Paquet
*Département de Chimie, Université de Montréal, C. P. 6128, Succursale
Centre-Ville, Montréal, Québec, Canada H3C 3J7, Email: helene.lebel
umontreal.ca
H. Lebel, V. Paquet, J. Am. Chem. Soc., 2004, 126, 320-328.
DOI: 10.1021/ja038112o (free Supporting Information)
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Abstract
A mild and nonbasic rhodium-catalyzed methylenation of aldehydes using trimethylsilyldiazomethane and triphenylphosphine in THF produces various terminal alkenes in excellent yields including enolizable keto aldehydes and nonracemic aldehydes. The use of an easily removable phosphine is also described.
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proposed mechanism
H. Lebel, M. Davi, S. Díez-Gonzlez, S. P. Nolan, J. Org. Chem., 2007, 72, 144-149.
Reductive One-Carbon Homologation of Aldehydes and Ketones
H. Lebel, C. Ladjel, J. Org. Chem., 2005, 70, 10159-10161.
Multicatalytic Processes Using Diverse Transition Metals for the Synthesis of Alkenes
H. Lebel, V. Paquet, J. Am. Chem. Soc., 2004, 126, 11152-11153.
Key Words
ID: J48-Y2004-1360
