Katalytische asymmetrische reduktive Kondensation von N‐H‐Iminen: Synthese von <i>C</i><sub>2</sub>‐symmetrischen sekundären Aminen

This work describes the use of cheap, safe, and easy‐to‐handle hydrosilatrane as the reductant in direct reductive amination reactions. This efficient method enables a facile, metal‐free access to secondary and tertiary amines from a wide range of aldehydes and ketones, with the synthesis of tertiary amines requiring no additives at all. This reaction demonstrates excellent functional group tolerance, chemoselectivity, and scalability.magnified image

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Simple Metal‐Free Direct Reductive Amination Using Hydrosilatrane to Form Secondary and Tertiary Amines

Varjosaari

Skrypai

Suating

et al. 2017

Adv Synth Catal

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Unified Synthesis of Polycyclic Alkaloids by Complementary Carbonyl Activation**

List

Christmann

2021

Angewandte Chemie

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A complementary dual carbonyl activation strategy for the synthesis of polycyclic alkaloids has been developed. Successful applications include the synthesis of tetracyclic alkaloids harmalanine, harmalacinine, pentacyclic indoloquinolizidine alkaloid nortetoyobyrine, and octacyclic β-carboline alkaloid peganumine A. The latter synthesis features a protecting-group-free assembly and an asymmetric disulfonimide catalyzed cyclization. Furthermore, formal syntheses of hirsutine, deplancheine, 10-desbromoarborescidine A, and oxindole alkaloids rhynchophylline and isorhynchophylline have been achieved. Finally, a concise synthesis of berberine alkaloid ilicifoline B was completed.

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An Iridium Catalytic System Compatible with Inorganic and Organic Nitrogen Sources for Dual Asymmetric Reductive Amination Reactions

Gao

Huang

et al. 2021

Angewandte Chemie

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Asymmetric reductive amination (ARA) is one of the most promising methods for the synthesis of chiral amines. Herein we report our efforts on merging two ARA reactions into a single-step transformation. Catalyzed by a complex formed from iridium and a steric hindered phosphoramidite, readily available and inexpensive aromatic ketones initially undergo the first ARA with ammonium acetate to afford primary amines, which serve as the amine sources for the second ARA, and finally provide the enantiopure C 2 -symmetric secondary amine products. The developed process competently enables the successive coupling of inorganic and organic nitrogen sources with ketones in the same reaction system. The Brønsted acid additive plays multiple roles in this procedure: it accelerates the formation of imine intermediates, minimizes the inhibitory effect of N-containing species on the iridium catalyst, and reduces the primary amine side products.Scheme 1. Nitrogen sources for asymmetric reductive amination.

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Katalytische asymmetrische reduktive Kondensation von N‐H‐Iminen: Synthese von C₂‐symmetrischen sekundären Aminen

Cited by 8 publications

References 83 publications

Simple Metal‐Free Direct Reductive Amination Using Hydrosilatrane to Form Secondary and Tertiary Amines

Simple Metal‐Free Direct Reductive Amination Using Hydrosilatrane to Form Secondary and Tertiary Amines

Unified Synthesis of Polycyclic Alkaloids by Complementary Carbonyl Activation**

An Iridium Catalytic System Compatible with Inorganic and Organic Nitrogen Sources for Dual Asymmetric Reductive Amination Reactions

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Katalytische asymmetrische reduktive Kondensation von N‐H‐Iminen: Synthese von C2‐symmetrischen sekundären Aminen

Cited by 8 publications

References 83 publications

Simple Metal‐Free Direct Reductive Amination Using Hydrosilatrane to Form Secondary and Tertiary Amines

Simple Metal‐Free Direct Reductive Amination Using Hydrosilatrane to Form Secondary and Tertiary Amines

Unified Synthesis of Polycyclic Alkaloids by Complementary Carbonyl Activation**

An Iridium Catalytic System Compatible with Inorganic and Organic Nitrogen Sources for Dual Asymmetric Reductive Amination Reactions

Contact Info

Product

Resources

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Katalytische asymmetrische reduktive Kondensation von N‐H‐Iminen: Synthese von C₂‐symmetrischen sekundären Aminen