183990-48-9Relevant articles and documents
Succinct synthesis of β-amino acids via chiral isoxazolines
Fuller, Amelia A.,Chen, Bin,Minter, Aaron R.,Mapp, Anna K.
, p. 5376 - 5383 (2007/10/03)
β-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 β-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 β-amino acid structural types with excellent selectivity. Of particular note is the use of this approach to prepare highly substituted cis-β-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.
Synthesis of Cyclic and Acyclic β-Amino Acids via Chelation-Controlled 1,3-Dipolar Cycloaddition
Hanselmann, Roger,Zhou, Jiacheng,Ma, Philip,Confalone, Pat N.
, p. 8739 - 8741 (2007/10/03)
Isoxazolidines have been synthesized in diastereomeric excess up to 94% via a MgBr2-induced chelation-controlled 1,3-dipolar cycloaddition reaction with N-hydroxyphenylglycinol as a chiral auxiliary. The diastereomerically pure isoxazolidines were further transformed into cyclic and acyclic β-amino acid derivatives.
Enantioselective conjugate addition of organomagnesium amides to enamidomalonates: Synthesis of either enantiomer of β-amino acid derivatives [18]
Sibi,Asano
, p. 9708 - 9709 (2007/10/03)
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