147700-92-3Relevant articles and documents
Asymmetric synthesis of α,α-disubstituted amino acids by diastereoselective functionalization of enantiopure phenyloxazinones, derivatives of asymmetric Strecker reaction products of aldehydes
Ding, Ke,Ma, Dawei
, p. 6361 - 6366 (2007/10/03)
Esterification of the asymmetric Strecker reaction products of a suitable aldehyde and (R)-phenylglycinol followed by lactonization and alkylation provides chiral oxazinones 5. Treatment of the enolates of 5 with active alkyl halides, or aldehydes provided the corresponding functionalization products with high diastereoselectivity. The configuration of newly created quaternary carbon is S for the products coupled with simple alkyl halides and aldehydes, and R for the products coupled with methyl bromoacetate. Deprotection of these products afforded the corresponding enantiopure α,α-dialkyl amino acids.
Synthesis of α-Alkyl-α-Benzyl Amino Acid Derivatives, via the Diastereoselective Alkylation of (3S,5R)-N,3-Dibenzyl-3,4,5,6-tetrahydro-5-phenyl-1,4-oxazin-2-one
Boa, Andrew N.,Guest, Amanda L.,Jenkins, Paul R.,Fawcett, John,Russell, David R.,Waterson, David
, p. 477 - 482 (2007/10/02)
(3S,5R)-N,3-Dibenzyl-3,4,5,6-tetrahydro-5-phenyl-1,4-oxazin-2-one, derived from L-phenylalanine and phenacyl bromide, was alkylated in a diastereoselective manner to give a range of α-alkylated phenylalanine derivatives.
