Pd-catalyzed reductive cleavage of N-N bond in dibenzyl-1-alkylhydrazine-1,2-dicarboxylates with PMHS: Application to a formal enantioselective synthesis of (R)-sitagliptin

Soumen Dey; Sunita K. Gadakh; Brij Bhushan Ahuja; Sanjay P. Kamble; Arumugam Sudalai

doi:10.1016/j.tetlet.2015.12.116

Pd-catalyzed reductive cleavage of N-N bond in dibenzyl-1-alkylhydrazine-1,2-dicarboxylates with PMHS: Application to a formal enantioselective synthesis of (R)-sitagliptin

Soumen Dey, Sunita K. Gadakh, Brij Bhushan Ahuja, Sanjay P. Kamble, Arumugam Sudalai^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

Abstract

An environmentally benign approach involving Pd-catalyzed reductive N-N bond cleavage in dibenzyl-1-alkylhydrazine-1,2-dicarboxylates leading to the synthesis of N-(tert-butoxy)carbamates under very mild conditions has been described. PMHS serves as an inexpensive source of hydride in MeOH/deionized H₂O medium. This protocol has been successfully applied in the formal synthesis of (R)-sitagliptin, an anti-diabetic drug.

Original language	English
Pages (from-to)	684-687
Number of pages	4
Journal	Tetrahedron Letters
Volume	57
Issue number	6
DOIs	https://doi.org/10.1016/j.tetlet.2015.12.116
State	Published - 10 Feb 2016
Externally published	Yes

Keywords

Environmentally benign
Hydrazine
PMHS
Reductive cleavage
anti-Diabetic

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1016/j.tetlet.2015.12.116

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abstract = "An environmentally benign approach involving Pd-catalyzed reductive N-N bond cleavage in dibenzyl-1-alkylhydrazine-1,2-dicarboxylates leading to the synthesis of N-(tert-butoxy)carbamates under very mild conditions has been described. PMHS serves as an inexpensive source of hydride in MeOH/deionized H2O medium. This protocol has been successfully applied in the formal synthesis of (R)-sitagliptin, an anti-diabetic drug.",

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AU - Dey, Soumen

AU - Gadakh, Sunita K.

AU - Ahuja, Brij Bhushan

AU - Kamble, Sanjay P.

AU - Sudalai, Arumugam

PY - 2016/2/10

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KW - Reductive cleavage

KW - anti-Diabetic

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Pd-catalyzed reductive cleavage of N-N bond in dibenzyl-1-alkylhydrazine-1,2-dicarboxylates with PMHS: Application to a formal enantioselective synthesis of (R)-sitagliptin

Abstract

Keywords

UN SDGs

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