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

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...

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Bibliographic Details
Published in:Organic chemistry frontiers an international journal of organic chemistry 2020-06, Vol.7 (11), p.1388-1394
Main Authors: Roy, Sourav, Pradhan, Suman, Kumar, Krishan, Chatterjee, Indranil
Format: Article
Language:English
Subjects:
Cascade chemical reactions
Complexity
Crystallography
Derivatives
Enantiomers
Organic chemistry
Quinones
Selectivity
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Summary: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.
ISSN:2052-4110
2052-4110
DOI:10.1039/d0qo00354a