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Synthesis of New Chiral N-alkyl Betti-base Ligands via One-Pot Three Component Strategy

[ Vol. 10 , Issue. 1 ]

Author(s):

Siva Ganesh, Kondabatini Sarika, Pedavenkatagari Narayana Reddy* and Pannala Padmaja*   Pages 75 - 80 ( 6 )

Abstract:


Background: Betti base derivatives were employed as chiral ligands or as chiral auxiliaries in asymmetric transformations. In particular, N-alkyl Betti base derivatives are gaining importance as excellent ligands in asymmetric reactions. However, no appropriate method exists for regioselective N-alkylation of Betti base. Therefore, there is an urgent need to develop a new protocol for the regioselective N-alkylation of chiral Betti-base.

Methods: An efficient method has been developed for one-pot synthesis of chiral N-alkyl Bettibase ligands from (S)-(+)-Betti base, arylglyoxals and cyclic 1,3-C,N-binucleophiles under catalyst- free conditions.

Results: The chiral N-alkyl Betti-base ligands were obtained in good yields with excellent enantioselectivities. This method is rapid, clean and does not require a catalyst or chromatographic purification.

Conclusion: We have developed an efficient one-pot three component strategy for the synthesis of new chiral N-alkyl Betti-base ligands from (S)-(+)-Betti base, arylglyoxals and cyclic 1,3-C,Nbinucleophiles in the absence of a catalyst.

Keywords:

Betti base, N-alkyl betti-base, arylglyoxals, 1, 3-C, N-binucleophiles, multicomponent reaction, asymmetric catalysis.

Affiliation:

Department of Chemistry, School of Science, Gitam University, Hyderabad (T.S), Department of Chemistry, School of Science, Gitam University, Hyderabad (T.S), Department of Chemistry, School of Science, Gitam University, Hyderabad (T.S), Centre for Semio Chemicals, CSIR-Indian Institute of Chemical Technology, Hyderabad

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