title: (L)-(Trimethylsilyl)alanine synthesis exploiting hydroxypinanone-induced diastereoselective alkylation.
abstract: A new and efficient synthesis of (L)-(trimethylsilyl)alanine (TMSAla) with suitable protection for use in Solid Phase Peptide Synthesis (SPPS) has been accomplished starting from glycine tert-butyl ester and using hydroxypinanone as chiral inductor. The silylated side chain was introduced by alkylation of the Schiff base intermediate with iodomethyl(trimethylsilane) at -78 °C. Among the different synthetic routes that were tested including several chiral inductors and different Schiff bases, this strategy was selected and afforded (L)-TMSAla in good chemical overall yield with 98 % ee.
authors.affiliation: IBMM, UMR-CNRS-5247, Universités Montpellier I and II, Place Eugène Bataillon, 34095 Montpellier, France.
authors.forename: A
authors.initials: A
authors.lastname: René
authors.forename: N
authors.initials: N
authors.lastname: Vanthuyne
authors.forename: J
authors.initials: J
authors.lastname: Martinez
authors.forename: F
authors.initials: F
authors.lastname: Cavelier
mesh_terms: D000409:Alanine / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D000478:Alkylation; D002384:Catalysis; D005998:Glycine / Q000031:analogs & derivatives / Q000737:chemistry; D015394:Molecular Structure; D012545:Schiff Bases / Q000737:chemistry; D013237:Stereoisomerism; D014297:Trimethylsilyl Compounds / Q000138:chemical synthesis*
chemical_list: D012545:Schiff Bases; D014297:Trimethylsilyl Compounds; C042193:glycine tert-butyl ester; D000409:Alanine; D005998:Glycine