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Issue 11, 2020
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Asymmetric organocatalytic double 1,6-addition: rapid access to chiral chromans with molecular complexity

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Abstract

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.

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

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Article information


Submitted
20 Mar 2020
Accepted
28 Apr 2020
First published
28 Apr 2020

Org. Chem. Front., 2020,7, 1388-1394
Article type
Research Article

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

S. Roy, S. Pradhan, K. Kumar and I. Chatterjee, Org. Chem. Front., 2020, 7, 1388
DOI: 10.1039/D0QO00354A

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