Selective reaction of camphor-derived exo-formyl [2.2.1]bicyclic carbinol with alkyl primary amines: application to the preparation of new chiral catalysts for asymmetric reduction of aryl ketones

The utility of camphor in the chemical sciences is vast and well documented, yet the creation of camphor‐derived potentially useful bicyclo[2.2.1]heptane scaffolds still remains one of the great challenges of synthetic organic chemistry. Herein, we show that CF3SO3H/(CF3CO)2O‐mediated acylation of camphor with benzoic acids is accompanied by a cascade of alkyl and hydride shifts and opens access to a new type of polyfunctional isoborneol. In case of salicylic acids, camphor feels the presence of the ortho‐hydroxy group in the aryl moiety, the influence of which provokes cleavage of the bicycloheptane skeleton to lead to monocyclic carvenone.

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Condensation‐ring Expansion Reaction of Formyl[2.2.1]bicyclic Carbinols with Para‐substituted Phenyl Amines: Application to the Preparation of [3.2.1]bicyclic N‐aryl‐1,2,3‐oxathiazolidine‐2‐oxide Agents

Yang

Chen

Kao

et al. 2012

J Chinese Chemical Soc

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Individual reaction of camphene-derived endo-formyl [2.2.1]bicyclic carbinol and that of camphor-derived exo-formyl[2.2.1]bicyclic carbinol with parent and para-substituted phenyl amines gave regio-and stereospecific corresponding [3.2.1]bicyclic (para-substituted) phenyl amino ketones. Mechanism of each reaction was discussed. Some camphor-derived [3.2.1]bicyclic amino ketones were reduced to [3.2.1]bicyclic (para-substituted) phenyl amino alcohols, which were then treated with mesyl chloride to provide [3.2.1]bicyclic N-phenyl/aryl-1,2,3-oxathiazolidine-2-oxide agents. The mechanism of this final reaction was discussed as well.

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Selective reaction of camphor-derived exo-formyl [2.2.1]bicyclic carbinol with alkyl primary amines: application to the preparation of new chiral catalysts for asymmetric reduction of aryl ketones

Cited by 9 publications

References 21 publications

ChemInform Abstract: Selective Reaction of Camphor‐Derived exo‐Formyl [2.2.1]Bicyclic Carbinol with Alkyl Primary Amines: Application to the Preparation of New Chiral Catalysts for Asymmetric Reduction of Aryl Ketones.

ChemInform Abstract: Selective Reaction of Camphor‐Derived exo‐Formyl [2.2.1]Bicyclic Carbinol with Alkyl Primary Amines: Application to the Preparation of New Chiral Catalysts for Asymmetric Reduction of Aryl Ketones.

Unknown Camphor: Regioselective Rearrangement under Acylation in a CF₃SO₃H/(CF₃CO)₂O System

Condensation‐ring Expansion Reaction of Formyl[2.2.1]bicyclic Carbinols with Para‐substituted Phenyl Amines: Application to the Preparation of [3.2.1]bicyclic N‐aryl‐1,2,3‐oxathiazolidine‐2‐oxide Agents

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Selective reaction of camphor-derived exo-formyl [2.2.1]bicyclic carbinol with alkyl primary amines: application to the preparation of new chiral catalysts for asymmetric reduction of aryl ketones

Cited by 9 publications

References 21 publications

ChemInform Abstract: Selective Reaction of Camphor‐Derived exo‐Formyl [2.2.1]Bicyclic Carbinol with Alkyl Primary Amines: Application to the Preparation of New Chiral Catalysts for Asymmetric Reduction of Aryl Ketones.

ChemInform Abstract: Selective Reaction of Camphor‐Derived exo‐Formyl [2.2.1]Bicyclic Carbinol with Alkyl Primary Amines: Application to the Preparation of New Chiral Catalysts for Asymmetric Reduction of Aryl Ketones.

Unknown Camphor: Regioselective Rearrangement under Acylation in a CF3SO3H/(CF3CO)2O System

Condensation‐ring Expansion Reaction of Formyl[2.2.1]bicyclic Carbinols with Para‐substituted Phenyl Amines: Application to the Preparation of [3.2.1]bicyclic N‐aryl‐1,2,3‐oxathiazolidine‐2‐oxide Agents

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Product

Resources

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Unknown Camphor: Regioselective Rearrangement under Acylation in a CF₃SO₃H/(CF₃CO)₂O System