145057-95-0Relevant academic research and scientific papers
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.
An Efficient and Practical Synthesis of L-α-Amino Acids Using (R)-Phenylglycinol as a Chiral Auxiliary
Inaba, Takashi,Kozono, Ichiro,Fujita, Makoto,Ogura, Katsuyuki
, p. 2359 - 2365 (2007/10/02)
L-α-Amino acids including L-α-arylglycines were conveniently and stereoselectively synthesized via the α-amino carbonitriles given by the Strecker reaction of (R)-2-amino-2-phenylethanol with aldehydes and hydrogen cyanide.The stereoselectivity of these α-amino carbonitriles was thermodynamically controlled.
