Synfacts 2008(2): 0189-0189  
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

Contributor(s): Paul Knochel, Tobias Thaler
N. Selander, A. Kipke, S. Sebelius, K. J. Szabó*
Stockholm University, Sweden
Further Information

Publication History

Publication Date:
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.