A concise approach to structurally diverse beta-amino acids.
We have demonstrated that the high yields and selectivities of 1,3-dipolar cycloadditions can be translated into facile stereoselective syntheses of a diverse array of beta-amino acids, key components of bioactive natural products, beta-lactams, and peptidomimetics. Simply by selecting different combinations of three readily available starting materials (an oxime, a chiral allylic alcohol, and a nucleophile), we used the reaction sequence to prepare four different beta-amino acid structural types with a variety of substitution patterns in good overall yield. Of particular note is the use of this approach to prepare highly substituted beta-amino acids not readily accessible by previously reported methodologies. This will pave the way for future studies of the structure and function of this important class of molecules.
Minter
Aaron R
AR
Department of Chemistry, University of Michigan, Ann Arbor, Michigan 48109, USA.
Fuller
Amelia A
AA
Mapp
Anna K
AK
D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D007555:Isoxazoles / Q000737:chemistry; D013237:Stereoisomerism
D000596:Amino Acids; D007555:Isoxazoles