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Synfacts 2024; 20(02): 0219
DOI: 10.1055/s-0043-1763664
DOI: 10.1055/s-0043-1763664
Peptide Chemistry
Synthesis of α-Quaternary Amino Esters via Intramolecular Rearrangement
Wilson MW,
*,
Ault-Justus SE,
Hodges JC,
Rubin JR.
Parke-Davis Pharmaceutical Research, Division of Warner-Lambert Company, Ann Arbor,
USA
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
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.
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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.
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Publication History
Article published online:
16 January 2024
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