Journal
ORGANIC CHEMISTRY FRONTIERS
Volume 7, Issue 11, Pages 1388-1394Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d0qo00354a
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Funding
- SERB, DST, India [ECR/2018/000098]
- IIT va
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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 Jorgensen-Hayashi organocatalysts are shown to catalyze the transformation of unbiased 2,4-dienals under mild reaction conditions with exclusive delta-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.
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