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Formation of Allyl Boronates and Their Direct Conver-sion into α-Amino Acids and Homoallyl Alcohols
N. Selander, A. Kipke, S. Sebelius, K. J. Szabó*
Stockholm University, Sweden
23 January 2008 (online)
Allyl boronic acids are more reactive allylating reagents than their boronate ester counterparts. However, isolation of these species is difficult as they rapidly decompose under solvent-free conditions. The authors have developed a way of generating allyl boronic acids in situ and of reacting them directly with aldehydes and ketones. Thus, this method gave a highly stereoselective access to homoallylic alcohols and unnatural α-amino acids.