Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 79, Issue 15, Pages 7141-7151Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo501293m
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Funding
- NSFC [21372002, 21232007]
- Open Foundation of Jiangsu Key Laboratory [K201314]
- PAPD
- Qing Lan Project of Jiangsu Province
- Graduate Students Project of Jiangsu Normal University [2014YZD012]
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The first organocatalytic asymmetric formal alkenylation of multicydic alcohols using non-metal-based alkenes instead of alkenyl metals as a source of an alkenyl group has been established via chiral phosphoric acid catalyzed tandem reactions. This transformation directly assembles isoindolo-beta-carboline-derived hydroxylactams with o-hydroxystyrenes via an asymmetric cascade vinylogous addition/hydrogen elimination reaction sequence, offering an easy access to functionalized chiral isoindolo-beta-carbolines with one quaternary stereogenic center in high chemo-, (E/Z)-, and enantioselectivities (up to >95:5 cr, >95:5 E/Z, 97:3 er). This approach also represents the first catalytic asymmetric formal alkenylation of isoindolo-beta-carbolinederived hydroxylactams, which provides a useful strategy for ffinctionalization of isoindolo-beta-carbolines and synthesis of chiral isoindolo-beta-carboline derivatives. In addition, the investigation on the activating mode revealed that the hydroxyl group in o-hydroxystyrene was essentially important for generating a hydrogen-bond interaction with the catalyst. The dual activation mode of hydrogen bond and ion pair between the catalyst and the substrates cooperatively facilitated the desired formal alkenylation reaction in a chemo- and stereoselective way.
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