Mechanistic details of amino acid catalyzed two-component Mannich reaction: experimental study backed by density functional calculations.

Abstract:

:The role of pH-dependent ionic structures of L-amino acids in catalysis has been investigated for the two-component Mannich reactions between dimethyl malonate (DMM)/ethyl acetoacetate (EAA) and imines. As catalysts, L-amino acids performed well, even better than corresponding base catalysts and provided the β-amino carbonyl compounds in very high yields. Density functional calculations were used to gain the mechanistic insight of the reaction. High catalytic efficiency of amino acids was attributed to the facile formation of carbanion intermediate through barrierless transition state TS1 (- 19.43 kcal/mol) and then its stabilization owing to carbanion interaction with protonated amino acid.

journal_name

Amino Acids

journal_title

Amino acids

authors

Rani D,Thakur L,Khera M,Goel N,Agarwal J

doi

10.1007/s00726-019-02798-z

subject

Has Abstract

pub_date

2019-11-01 00:00:00

pages

1609-1621

issue

10-12

eissn

0939-4451

issn

1438-2199

pii

10.1007/s00726-019-02798-z

journal_volume

51

pub_type

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