Enantioselective Synthesis of cis-Decalins Using Organocatalysis and Sulfonyl Nazarov Reagents

A step- and atom-economical protocol allowing the synthesis of 1,4-diazepanes and also tetrahydro- and decahydro-1,5-benzodiazepines is described. The method proceeds from very simple starting materials such as 1,2-diamines and alkyl 3-oxohex-5-enoates and can be performed under solvent-free conditions in many instances. The key event of this process was the generation in situ of an aza-Nazarov reagent and its subsequent intramolecular aza-Michael cyclization. An intermolecular version of the reaction was also established and applied to the synthesis of the first example of the pyrrolo[1,2-a][1,5]diazonine framework.

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Synthesis of 1,4-Diazepanes and Benzo[b][1,4]diazepines by a Domino Process Involving theIn SituGeneration of an Aza-Nazarov Reagent

Maiti

Leonardi

Cores

et al. 2020

J. Org. Chem.

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A triple cascade approach towards the diastereoselective synthesis of spiro trans-decalinol scaffolds

Settipalli

Anwar

2022

Chem. Commun.

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Enantioselective Synthesis of cis-Decalins Using Organocatalysis and Sulfonyl Nazarov Reagents

Abstract: The first organocatalytic synthesis of cis-decalins using sulfonyl Nazarov reagents is reported. The Jørgensen’s catalyst directs this highly enantioselective synthesis using different cyclohexenal derivatives.

Cited by 2 publications

References 21 publications

Synthesis of 1,4-Diazepanes and Benzo[b][1,4]diazepines by a Domino Process Involving theIn SituGeneration of an Aza-Nazarov Reagent

Synthesis of 1,4-Diazepanes and Benzo[b][1,4]diazepines by a Domino Process Involving theIn SituGeneration of an Aza-Nazarov Reagent

A triple cascade approach towards the diastereoselective synthesis of spiro trans-decalinol scaffolds

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