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DOI: 10.1055/s-0043-1763664
Synthesis of α-Quaternary Amino Esters via Intramolecular Rearrangement
A Facile Rearrangement of N-Alkyl, N-(o or p-Nitrophenylsulfonamide)-α-Amino Esters.
Tetrahedron 1999;
55: 1647-1656
DOI: 10.1016/S0040-4020(98)01209-5
Key words
α-quaternary amino esters - intramolecular rearrangement - Meisenheimer intermediate - tetrabutylammonium hydroxide
Significance
α-Quaternary amino acids are ubiquitously found in many biologically active molecules and play a crucial role in the determination of various biological pathways of metabolism. In 1999, the authors developed a tetrabutylammonium hydroxide-mediated intramolecular rearrangement of N-alkyl, N-(o- or p-nitrophenylsulfonamide)-α-amino esters for the synthesis of α-quaternary amino acids esters.
Comment
A series of α-quaternary amino acids esters were synthesized via a Meisenheimer intermediate. The reaction proceeded with good to moderate yields and with good selectivity.
Publikationsverlauf
Artikel online veröffentlicht:
16. Januar 2024
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