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Synthesis of α-heterosubstituted glycine derivatives from dihaloethanamides

✍ Scribed by Patrick D. Bailey; S.Richard Baker; Andrew N. Boa; Joanne Clayson; Georgina M. Rosair

Book ID
104259961
Publisher
Elsevier Science
Year
1998
Tongue
French
Weight
258 KB
Volume
39
Category
Article
ISSN
0040-4039

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✦ Synopsis

A range of protected ct-heterosubstituted analogues of glycine were synthesised from starting materials of the type CHFX-CONHR [X = CI, Br, I; R = CH2Ph, (S)-CHMePh]; the final products included derivatives of glycine possessing N, O, F or S in the c-position, and the first example of a free a-fluoro-a-amino acid (ctfluorobetaine) whose structure was confirmed by X-ray crystal structure determination.

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3-Aminoaspartic acid derivatives 3 have been synthesized via stereoselective alkylation of a-acetyloxyglycine Schiff base 2 with the enolate of glycine anion equivalent 1 as a carbon nucleophile in the presence of Pd(OAc) 2 and BINAP at room temperature. High chemical yields and moderate stereoselec