Diastereoselective Synthesis of 3-Alkylindoloquinolizine Derivatives via Regiospecific Oxidative Cyclization

Juárez, Jorge R.; Morales-Barba, Susana; Terán, Joel L.; Gnecco, Dino; Orea, María L.; Aparicio, David M.; Gómez-Calvario, Víctor

doi:10.3987/com-19-14058

Cited by 4 publications

(1 citation statement)

References 12 publications

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“…The potential utility of this protocol was further demonstrated through the formal synthesis of several targets of wide interest. Hydrogenation of 2l catalyzed by Pd/C and subsequential Ts-deprotection afforded compound 6, a key intermediate in Juaŕez's synthesis of 3-ethylindoloquinolizine, 18 in 89% overall yield. Using Wilkinson hydrogenation under a H 2 atmosphere, 2e and 2g could be, respectively, converted into 3-arylpeperidines 7e and 7g in quantitative yield and with no erosion of enantioselectivity.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Domino Sequences Involving Stereoselective Hydrazone-Type Heck Reaction and Denitrogenative [1,5]-Sigmatropic Rearrangement

Zhou

et al. 2023

J. Am. Chem. Soc.

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Although the Heck reactions of alkene partners with various electrophiles have achieved great success, the variant focused on carbon�heteroatom counterparts still remains elusive. Herein, we report a Pd(0)-catalyzed asymmetric intramolecular hydrazone-type Heck reaction of N-[(Z)-3-iodoallyl]-aminoacetaldehyde and hydrazine hydrate (NH 2 NH 2 −H 2 O), wherein the required hydrazone is in situ generated via an acid-promoted condensation. A key strategic advantage of this Heck paradigm is that the resultant Heck product allylic diazene rapidly undergoes stereospecific denitrogenative [1,5]-sigmatropic rearrangement, eventually furnishing a domino sequence toward 3-substituted tetrahydropyridine (THP) with high enantioselectivity. The substrate-induced diastereoselective version has also been realized, exclusively giving cis-2,5-disubstituted THPs. The utility of this sequence is demonstrated by the formal synthesis of multiple valuable bioactive targets, including 3-ethylindoloquinolizine, preclamol, and niraparib.

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Section: ■ Results and Discussionmentioning

confidence: 99%

Domino Sequences Involving Stereoselective Hydrazone-Type Heck Reaction and Denitrogenative [1,5]-Sigmatropic Rearrangement

Zhou

et al. 2023

J. Am. Chem. Soc.

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Access to 1,3‐Dinitriles by Enantioselective Auto‐tandem Catalysis: Merging Allylic Cyanation with Asymmetric Hydrocyanation

Long

Gao

et al. 2020

Angewandte Chemie

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Enantioselective auto‐tandem catalysis represents a challenging yet highlight attractive topic in the field of asymmetric catalysis. In this context, we describe a dual catalytic cycle that merges allylic cyanation and asymmetric hydrocyanation. The one‐pot conversion of a broad array of allylic alcohols into their corresponding 1,3‐dinitriles proceeds in good yield with high enantioselectivity. The products are densely functionalized and can be easily transformed to chiral diamines, dinitriles, diesters, and piperidines. Mechanistic studies clearly support a novel sequential cyanation/hydrocyanation pathway.

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Access to 1,3‐Dinitriles by Enantioselective Auto‐tandem Catalysis: Merging Allylic Cyanation with Asymmetric Hydrocyanation

Long

Gao

et al. 2020

Angew Chem Int Ed

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Diastereoselective Synthesis of 3-Alkylindoloquinolizine Derivatives via Regiospecific Oxidative Cyclization

Abstract: 3-Alkylindoloquinolizine alkaloids were synthetized in two steps from enantiopure 3-alkylpiperidines through sequential N-alkylation and regiospecific and diastereoselective oxidative cyclization.

Cited by 4 publications

References 12 publications

Domino Sequences Involving Stereoselective Hydrazone-Type Heck Reaction and Denitrogenative [1,5]-Sigmatropic Rearrangement

Domino Sequences Involving Stereoselective Hydrazone-Type Heck Reaction and Denitrogenative [1,5]-Sigmatropic Rearrangement

Access to 1,3‐Dinitriles by Enantioselective Auto‐tandem Catalysis: Merging Allylic Cyanation with Asymmetric Hydrocyanation

Access to 1,3‐Dinitriles by Enantioselective Auto‐tandem Catalysis: Merging Allylic Cyanation with Asymmetric Hydrocyanation

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