Synthesis of β-chloro α-amino acids: (2 S,3 R)- and (2 S,3 S)-3-chloroleucine

• Published in: Tetrahedron letters Vol. 47; no. 22; pp. 3701 - 3705
• Main Authors: Valls, Nativitat, Borregán, Mar, Bonjoch, Josep
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 29.05.2006; Elsevier
• Subjects: 3-Chloroleucine; Aeruginosins; Chemistry; Chemistry, Organic; Physical Sciences; Ring opening; Science & Technology; β-Chloro α-amino acids; β-Lactones; β-Lactones; Aeruginosins; 3-Chloroleucine; β-Chloro α-amino acids; Ring opening; ENANTIOSELECTIVE SYNTHESIS; AERUGINOSIN 298-A; 3-chloroleucine; L-THREONINE; beta-lactones; ring opening; SERINE; LACTONES; SALINOSPORAMIDE-A; aeruginosins; beta-chloro alpha-amino acids; CYSTEINE PROTEINASE-INHIBITORS; DERIVATIVES; EFFICIENT; STEREOCONTROLLED SYNTHESIS
• ISSN: 0040-4039; 1873-3581
• DOI: 10.1016/j.tetlet.2006.03.127

The same sequence was carried out using (2 R,3 R)-3-hydroxyleucine leading to the epimeric (2 S,3 S)-3-chloroleucine. The first syntheses of (2 S,3 R)- and (2 S,3 S)-3-chloroleucine (3-chloro- d-leucines 1 and 2) have been achieved from d-3-hydroxyleucine and allo- d-3-hydroxyleucine, respectively, through the formation of the corresponding N-Cbz β-lactones, followed by a ring opening promoted by lithium chloride and a debenzylation process.