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Synfacts 2008(2): 0189-0189
DOI: 10.1055/s-2007-992469
DOI: 10.1055/s-2007-992469
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York
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
Further Information
Publication History
Publication Date:
23 January 2008 (online)

Significance
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.