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 Acidsjournal_title
Amino acidsauthors
Rani D,Thakur L,Khera M,Goel N,Agarwal Jdoi
10.1007/s00726-019-02798-zsubject
Has Abstractpub_date
2019-11-01 00:00:00pages
1609-1621issue
10-12eissn
0939-4451issn
1438-2199pii
10.1007/s00726-019-02798-zjournal_volume
51pub_type
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