Asymmetric Synthesis of α‐Methyl α‐Amino Acids by Diastereoselective Alkylation of Optically Active 6‐Isopropyl‐3‐methyl‐2,3—dihydro‐6 H ‐1,4‐oxazin‐2‐ones | Zendy

Chinchilla Rafael | Zendy; Falvello Larry R. | Zendy; Galindo Nuria | Zendy; Nájera Carmen | Zendy

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Asymmetric Synthesis of α‐Methyl α‐Amino Acids by Diastereoselective Alkylation of Optically Active 6‐Isopropyl‐3‐methyl‐2,3—dihydro‐6 H ‐1,4‐oxazin‐2‐ones

Author(s) -

Chinchilla Rafael,

Falvello Larry R.,

Galindo Nuria,

Nájera Carmen

Publication year - 1997

Publication title -

angewandte chemie international edition in english

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 0570-0833

DOI - 10.1002/anie.199709951

Subject(s) - alkylation , isopropyl , chemistry , catalysis , hydrolysis , optically active , alanine , amino acid , stereochemistry , organic chemistry , medicinal chemistry , biochemistry

At room temperature already highly diastereoselective alkylation of the new, cyclic, chiral alanine ester derivatives (6 R )‐ 1 can been achieved with either K 2 CO 3 as base under solid–liquid phase‐transfer catalysis or Pd catalysis unter neutral conditions. The products (3 S ,6 R )‐ 2 can be easily hydrolyzed to form ( S )‐α‐methyl α‐amino acids.

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