Efficient diastereoselective synthesis of cis-2-amino-1-indanol derivatives and cis- and trans-1-amino-2-indanol via Pd-catalyzed hydrogenation

Nguyen, Thi Ha; Ma, Eunsook

doi:10.1080/00397911.2021.1989595

Cited by 2 publications

(1 citation statement)

References 26 publications

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“…Direct reduction of 1,2-indanedion-1-oxime ( 66 )—prepared from 2-indanone ( 4 ) via oximination—with H 2 in the presence of Pd/BaSO 4 led to the corresponding racemic cis - N -hydroxyamine 67 ( Scheme 26 A) [ 85 ]. Subsequent hydrogenation of the N -hydroxyamine moiety enabled (−/+)- 1 .…”

Section: Syntheses From Indane Skeletonmentioning

confidence: 99%

Strategies for Accessing cis-1-Amino-2-Indanol

Mendas,

Gastaldi,

Suppo

2024

Molecules

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cis-1-amino-2-indanol is an important building block in many areas of chemistry. Indeed, this molecule is currently used as skeleton in many ligands (BOX, PyBOX…), catalysts and chiral auxiliaries. Moreover, it has been incorporated in numerous bioactive structures. The major issues during its synthesis are the control of cis-selectivity, for which various strategies have been devised, and the enantioselectivity of the reaction. This review highlights the various methodologies implemented over the last few decades to access cis-1-amino-2-indanol in racemic and enantioselective manners. In addition, the various substitution patterns on the aromatic ring and their preparations are listed.

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Section: Syntheses From Indane Skeletonmentioning

confidence: 99%

Strategies for Accessing cis-1-Amino-2-Indanol

Mendas,

Gastaldi,

Suppo

2024

Molecules

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Synthesis of Spiropyrrolines via One-Pot Tf₂O-Mediated Amide Activation/Formal [3 + 2]-Cycloaddition of α-Formylamino Ketones

Ho,

Pierce

2024

J. Org. Chem.

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An efficient method for the synthesis of spiropyrrolines from readily accessible α-formylamino ketones is reported. The method involves amide activation using Tf 2 O, followed by a formal [3 + 2]-cycloaddition of the resulting enolic nitrilium intermediate with Michael acceptors, ultimately affording spiropyrrolines. Mechanistic insights were gained through NMR studies, elucidating the precise role of the base additive and suggesting the formation of an enolic nitrilium intermediate.

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Efficient diastereoselective synthesis of cis-2-amino-1-indanol derivatives and cis- and trans-1-amino-2-indanol via Pd-catalyzed hydrogenation

Cited by 2 publications

References 26 publications

Strategies for Accessing cis-1-Amino-2-Indanol

Strategies for Accessing cis-1-Amino-2-Indanol

Synthesis of Spiropyrrolines via One-Pot Tf₂O-Mediated Amide Activation/Formal [3 + 2]-Cycloaddition of α-Formylamino Ketones

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Efficient diastereoselective synthesis of cis-2-amino-1-indanol derivatives and cis- and trans-1-amino-2-indanol via Pd-catalyzed hydrogenation

Cited by 2 publications

References 26 publications

Strategies for Accessing cis-1-Amino-2-Indanol

Strategies for Accessing cis-1-Amino-2-Indanol

Synthesis of Spiropyrrolines via One-Pot Tf2O-Mediated Amide Activation/Formal [3 + 2]-Cycloaddition of α-Formylamino Ketones

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Synthesis of Spiropyrrolines via One-Pot Tf₂O-Mediated Amide Activation/Formal [3 + 2]-Cycloaddition of α-Formylamino Ketones