- Asymmetric synthesis of α,α-disubstituted amino acids by diastereoselective functionalization of enantiopure phenyloxazinones, derivatives of asymmetric Strecker reaction products of aldehydes
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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.
- Ding, Ke,Ma, Dawei
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p. 6361 - 6366
(2007/10/03)
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- Synthesis of enantiopure α,α-disubstituted amino acids from the asymmetric strecker reaction products of aldehydes
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(equation presented) Treatment of the enolates of 4 generated from the asymmetric Strecker reaction products with alkyl halides or aldehydes provided the corresponding functionalized products with high diastereoselectivity. Deprotection of these products
- Ma, Dawei,Ding, Ke
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p. 2515 - 2517
(2007/10/03)
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- 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
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(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.
- Boa, Andrew N.,Guest, Amanda L.,Jenkins, Paul R.,Fawcett, John,Russell, David R.,Waterson, David
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p. 477 - 482
(2007/10/02)
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