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
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.
