Synthesis of α-Quaternary Amino Esters via Intramolecular Rearrangement

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.

Publication History

Article published online:
16 January 2024