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Enantioselective synthesis of the tetrahydro-6H-benzo[c]chromenes via Domino Michael–Aldol condensation: control of five stereocenters in a quadruple-cascade organocatalytic multi-component reaction

✍ Scribed by Prakash Kotame; Bor-Cherng Hong; Ju-Hsiou Liao

Publisher
Elsevier Science
Year
2009
Tongue
French
Weight
307 KB
Volume
50
Category
Article
ISSN
0040-4039

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✦ Synopsis

Organocatalytic domino oxa-Michael-Michael-Michael-aldol condensation of 2-((E)-2-nitrovinyl)phenol and 2 equiv of a,b-unsaturated aldehydes (e.g., cinnamaldehyde) provided tetrahydro-6Hbenzo[c]chromenes in high diastereoselectivity and high enantioselectivity (>99% ee). Structure of the adduct 4a was confirmed unambiguously by X-ray analysis. The diversity of the protocol was demonstrated by the chemo-differentiating three-component reactions (ABC type) affording the highly functionalized tetrahydro-6H-benzo[c]chromenes.

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ChemInform Abstract: Enantioselective Sy
ChemInform Abstract: Enantioselective Synthesis of the Tetrahydro-6H-benzo[c]chromenes via Domino Michael—Aldol Condensation: Control of Five Stereocenters in a Quadruple-Cascade Organocatalytic Multi-Component Reaction.
✍ Prakash Kotame; Bor-Cherng Hong; Ju-Hsiou Liao 📂 Article 📅 2009 🏛 John Wiley and Sons ⚖ 32 KB 👁 1 views

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