Asymmetric synthesis of N-protected chiral 1-aminoalkylphosphonic acids and synthesis of side chain–functionalized depsiphosphonopeptides
✍ Scribed by Han Liu; Shuzong Cai; Jiaxi Xu
- Publisher
- John Wiley and Sons
- Year
- 2006
- Tongue
- English
- Weight
- 100 KB
- Volume
- 12
- Category
- Article
- ISSN
- 1075-2617
- DOI
- 10.1002/psc.731
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✦ Synopsis
Optically active 1-aminoalkylphosphonic acid derivatives were synthesized in moderate yields and optical purities via Mannich-type reactions of benzyl carbamate, aldehydes, and optically pure chlorophosphites. Side chain-functionalized depsiphosphonopeptides were also prepared in satisfactory yields directly from one-pot reactions of benzyl carbamate, aldehydes, and diethyl (R,R)-2-chloro-1,3,2-dioxaphospholane-4,5-dicarboxylate.
📜 SIMILAR VOLUMES
## Abstract __N__,__N__′‐Alkylidenebisamides 1, totally unsuitable as amidoalkylating agents toward phosphorous acid, react with its “activated” form prepared “in situ” from phosphorus(III) chloride and acetic acid to give the desired 1‐aminoalkylphosphonic acids 2 in high yields.
## Abstract Coupling of various acylated amino acid derivatives with (naphthalen‐2‐lyloxy)acetic acid (**3**) in the presence of 1‐hydroxy‐benzoteriazole (HOBt) and DCC afforded the new amides **6–12**. Alternatively, the latter compounds were prepared from reaction of the corresponding hydrazide *