Synthesis of tetrazole analogs of α-amino acids by alkylation of a Schiff base of α-aminomethyltetrazole
✍ Scribed by Yoshitaka Satoh; Stéphane De Lombaert; Nicholas Marcopulos; John Moliterni; Michael Moskal; Jenny Tan; Eli Wallace
- Publisher
- Elsevier Science
- Year
- 1998
- Tongue
- French
- Weight
- 199 KB
- Volume
- 39
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
A benzophenone imine of N-1 protected ct-aminomethyltetrazoles was found to undergo alkylation with organic halide:; in good yields. Deprotection afforded tetrazole analogs of a-amino acids.
📜 SIMILAR VOLUMES
A new general method of resolution of &\_-amino acids via their Schiff bases with 2-hydroxy pinan-3-ones is described. It complements the asymmetric synthesis of o(-disubstituted amino acids by alkylation of the Schiff bases. Asymmetric synthesis methods1'2 seldom give enantiomerically pure amino a
A short and convenient asymmetric synthesis of cl-alkyl a-amino acids is described, using (S)(-)-I-dimethoxymethyl-Z-methoxymethyl pyrrolidine (5) as chiral auxiliary reagent.
Y, 6 -Unsaturated a -amino phosphonic acids are obtained by alkylation of Schiff bases 2, 3 in the presence of a palladium catalyst under neutral or basic conditions in THF or DME, using allylic carbonates, esters or halides (50 -80 8 yields).