Chiron approach and the [4 + 2] Diels-Alder cycloaddition of 2-pyrones for the synthesis of cis-(-)-aminoindan-2-ol

Rosa-Barrales, Arturo de la; Pérez-Bautista, José Alvano; Cruz‐Gregorio, Silvano; Meza-León, Rosa L.; Quintero, Leticia; Cortezano-Arellano, Omar; Sartillo‐Piscil, Fernando

doi:10.1016/j.rechem.2021.100174

Cited by 2 publications

(1 citation statement)

References 16 publications

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“…In 2021, a successful enantioselective synthesis of cis -1-amino-2-indanol using the Diels–Alder reaction as a key step was reported ( Scheme 28 ) [ 89 ]. The chiral pool employed for the synthesis was the versatile chiron 7,3-xylofuranose derivative (7,3-LXF) prepared in two steps from diacetone-D-glucose [ 90 ].…”

Section: Syntheses From Non-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 Non-indane Skeletonmentioning

confidence: 99%

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

Mendas,

Gastaldi,

Suppo

2024

Molecules

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A Brief Review on Recent Developments in Diels-alder Reactions

Chaudhary,

Shaik,

Magan

et al. 2025

COS

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The [4+2] Diels-Alder cycloaddition has been widely used for the synthesis of six-mem-ber scaffolds. In recent years, there have been significant developments in this area, including the discovery and design of novel dienes and dienophiles with improved reactivity and selectivity. These new building blocks can be used to develop diverse molecular structures with functional group compatibility. Additionally, there is the use of catalytic systems and metal-mediated reactions to enable asymmetric [4+2] cycloadditions, resulting in enantiomerically enriched products. Over-all, recent studies related to [4+2] Diels-Alder cycloaddition using numerous dienes, dienophiles, and catalysts in different reaction conditions have significantly improved the efficiency, selectivity, and versatility of the reaction, making it an increasingly important tool in the synthesis of complex organic molecules as presented in this review. These advancements offer exciting possibilities for the development of new methods and reagents for the construction of six-membered rings and the synthesis of bioactive compounds.

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Chiron approach and the [4 + 2] Diels-Alder cycloaddition of 2-pyrones for the synthesis of cis-(-)-aminoindan-2-ol

Cited by 2 publications

References 16 publications

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

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

A Brief Review on Recent Developments in Diels-alder Reactions

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