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
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.
