Synthesis of novel phase transfer catalysts derived from proline-mandelic acid/tartaric acid: their evaluation in enantioselective epoxidation and Darzen condensation

Deepak P. Mahajan, Himanshu M. Godbole, Girij P. Singh, Gautham G. Shenoy

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

Abstract : Herein, we have described the synthesis of novel chiral cyclic phase transfer catalysts (PTCs). These catalysts are synthesized from proline, mandelic acid and tartaric acid by using simple synthetic methods with competitive yields. These chiral cyclic phase transfer catalysts have been characterized by 1 H NMR and 13 C NMR spectroscopy, IR spectroscopy and elemental analysis. The effectiveness of these novel chiral cyclic phase transfer catalysts was evaluated by applying them in the enantioselective epoxide synthesis from α , β unsaturated ketone (chalcone) and Darzens condensation. The obtained results show that the synthesized derivatives of proline, mandelic acid and tartaric acid are effectual as PTCs. Graphical Abstract: SYNOPSIS This paper shares the synthesis and characterization of novel chiral phase transfer catalysts from proline, mandelic acid and tartaric acid. The synthesis of these newly explored cyclic derivatives is reported by using a simple method with competitive yields. The effectiveness of these novel chiral cyclic phase transfer catalysts was evaluated by applying them in enantioselective epoxide synthesis from α, β unsaturated chalcone and in Darzen condensation. The obtained results show that the synthesized derivatives of proline, mandelic acid and tartaric acid are effectual as PTCs and useful towards the synthesis of enantioselective epoxide. [Figure not available: see fulltext.].

Original languageEnglish
Article number22
JournalJournal of Chemical Sciences
Volume131
Issue number3
DOIs
Publication statusPublished - 01-03-2019

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Epoxidation
Proline
Condensation
Catalysts
Epoxy Compounds
Chalcone
Derivatives
tartaric acid
mandelic acid
Ketones
Nuclear magnetic resonance spectroscopy
Infrared spectroscopy
Nuclear magnetic resonance
Chemical analysis

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

Cite this

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title = "Synthesis of novel phase transfer catalysts derived from proline-mandelic acid/tartaric acid: their evaluation in enantioselective epoxidation and Darzen condensation",
abstract = "Abstract : Herein, we have described the synthesis of novel chiral cyclic phase transfer catalysts (PTCs). These catalysts are synthesized from proline, mandelic acid and tartaric acid by using simple synthetic methods with competitive yields. These chiral cyclic phase transfer catalysts have been characterized by 1 H NMR and 13 C NMR spectroscopy, IR spectroscopy and elemental analysis. The effectiveness of these novel chiral cyclic phase transfer catalysts was evaluated by applying them in the enantioselective epoxide synthesis from α , β unsaturated ketone (chalcone) and Darzens condensation. The obtained results show that the synthesized derivatives of proline, mandelic acid and tartaric acid are effectual as PTCs. Graphical Abstract: SYNOPSIS This paper shares the synthesis and characterization of novel chiral phase transfer catalysts from proline, mandelic acid and tartaric acid. The synthesis of these newly explored cyclic derivatives is reported by using a simple method with competitive yields. The effectiveness of these novel chiral cyclic phase transfer catalysts was evaluated by applying them in enantioselective epoxide synthesis from α, β unsaturated chalcone and in Darzen condensation. The obtained results show that the synthesized derivatives of proline, mandelic acid and tartaric acid are effectual as PTCs and useful towards the synthesis of enantioselective epoxide. [Figure not available: see fulltext.].",
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Synthesis of novel phase transfer catalysts derived from proline-mandelic acid/tartaric acid : their evaluation in enantioselective epoxidation and Darzen condensation. / Mahajan, Deepak P.; Godbole, Himanshu M.; Singh, Girij P.; Shenoy, Gautham G.

In: Journal of Chemical Sciences, Vol. 131, No. 3, 22, 01.03.2019.

Research output: Contribution to journalArticle

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AU - Singh, Girij P.

AU - Shenoy, Gautham G.

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N2 - Abstract : Herein, we have described the synthesis of novel chiral cyclic phase transfer catalysts (PTCs). These catalysts are synthesized from proline, mandelic acid and tartaric acid by using simple synthetic methods with competitive yields. These chiral cyclic phase transfer catalysts have been characterized by 1 H NMR and 13 C NMR spectroscopy, IR spectroscopy and elemental analysis. The effectiveness of these novel chiral cyclic phase transfer catalysts was evaluated by applying them in the enantioselective epoxide synthesis from α , β unsaturated ketone (chalcone) and Darzens condensation. The obtained results show that the synthesized derivatives of proline, mandelic acid and tartaric acid are effectual as PTCs. Graphical Abstract: SYNOPSIS This paper shares the synthesis and characterization of novel chiral phase transfer catalysts from proline, mandelic acid and tartaric acid. The synthesis of these newly explored cyclic derivatives is reported by using a simple method with competitive yields. The effectiveness of these novel chiral cyclic phase transfer catalysts was evaluated by applying them in enantioselective epoxide synthesis from α, β unsaturated chalcone and in Darzen condensation. The obtained results show that the synthesized derivatives of proline, mandelic acid and tartaric acid are effectual as PTCs and useful towards the synthesis of enantioselective epoxide. [Figure not available: see fulltext.].

AB - Abstract : Herein, we have described the synthesis of novel chiral cyclic phase transfer catalysts (PTCs). These catalysts are synthesized from proline, mandelic acid and tartaric acid by using simple synthetic methods with competitive yields. These chiral cyclic phase transfer catalysts have been characterized by 1 H NMR and 13 C NMR spectroscopy, IR spectroscopy and elemental analysis. The effectiveness of these novel chiral cyclic phase transfer catalysts was evaluated by applying them in the enantioselective epoxide synthesis from α , β unsaturated ketone (chalcone) and Darzens condensation. The obtained results show that the synthesized derivatives of proline, mandelic acid and tartaric acid are effectual as PTCs. Graphical Abstract: SYNOPSIS This paper shares the synthesis and characterization of novel chiral phase transfer catalysts from proline, mandelic acid and tartaric acid. The synthesis of these newly explored cyclic derivatives is reported by using a simple method with competitive yields. The effectiveness of these novel chiral cyclic phase transfer catalysts was evaluated by applying them in enantioselective epoxide synthesis from α, β unsaturated chalcone and in Darzen condensation. The obtained results show that the synthesized derivatives of proline, mandelic acid and tartaric acid are effectual as PTCs and useful towards the synthesis of enantioselective epoxide. [Figure not available: see fulltext.].

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