Asymmetric organocatalytic double 1,6-addition: rapid access to chiral chromans with molecular complexity

文献情報

出版日 2020-04-28

DOI 10.1039/D0QO00354A

インパクトファクター 5.281

著者

Sourav Roy, Suman Pradhan, Krishan Kumar, Indranil Chatterjee

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要旨

An organocatalytic cascade vinylogous double 1,6-addition strategy for the synthesis of chiral chroman derivatives is reported. The cascade reaction follows oxa-Michael/1,6-addition reactions between ortho-hydroxyphenyl-substituted para-quinone methides and 2,4-dienal derivatives to deliver chroman derivatives with excellent yields (up to 96%) and stereoselectivities (up to >20 : 1 dr, >99% ee). The chiral secondary amine-based Jørgensen–Hayashi organocatalysts are shown to catalyze the transformation of unbiased 2,4-dienals under mild reaction conditions with exclusive δ-site selectivity and high control over enantioselectivity at a remote position. The synthetic transformations of the products ensure molecular complexity with a great level of enantiocontrol.

掲載誌

Organic Chemistry Frontiers

CiteScore: 7.8

自己引用率: 8.7%

年間論文数: 724

Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry

Asymmetric organocatalytic double 1,6-addition: rapid access to chiral chromans with molecular complexity

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