Succinct synthesis of beta-amino acids via chiral isoxazolines.
beta-Amino acids are important synthetic targets due to their presence in a wide variety of natural products, pharmaceutical agents, and mimics of protein structural motifs. While beta-amino acids containing geminal substitution patterns have enormous potential for application in these contexts, synthetic challenges to the stereoselective preparation of this class of compound have thus far limited more complete studies. We present here a straightforward method employing chiral isoxazolines as key intermediates to access five different beta-amino acid structural types with excellent selectivity. Of particular note is the use of this approach to prepare highly substituted cis-beta-proline analogues. The ready access to these diversely substituted compounds is expected to facilitate future studies of the structure and function of this important class of molecules.
Fuller
Amelia A
AA
Department of Chemistry, University of Michigan, Ann Arbor, Michigan 48109-1055, USA.
Chen
Bin
B
Minter
Aaron R
AR
Mapp
Anna K
AK
D000596:Amino Acids / Q000138:chemical synthesis*; D007555:Isoxazoles / Q000737:chemistry*; D008968:Molecular Conformation; D011392:Proline / Q000138:chemical synthesis; D013237:Stereoisomerism
D000596:Amino Acids; D007555:Isoxazoles; D011392:Proline