Organocatalytic Cascade Reactions: Towards the Diversification of Hydroisochromenes and Chromenes through Two Different Activation Modes

• Published in: Chemistry : a European journal Vol. 20; no. 36; pp. 11331 - 11335
• Main Authors: Cruz Cruz, David, Mose, Rasmus, Villegas Gómez, Clarisa, Torbensen, Stine V., Larsen, Martin S., Jørgensen, Karl Anker
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 01.09.2014; WILEY‐VCH Verlag; Wiley; Wiley Subscription Services, Inc
• Subjects: Activation; Alcohols; aminocatalysis; asymmetric catalysis; Cascade chemical reactions; cascade reactions; Chemistry; Chemistry, Multidisciplinary; chromenes hydroisochromenes; Diversification; Physical Sciences; Science & Technology; TANDEM REACTIONS; chromenes hydroisochromenes; DIELS-ALDER REACTIONS; TRIENAMINES; asymmetric catalysis; FORMAL 2+2 CYCLOADDITION; cascade reactions; 2,4-DIENALS; CONSTRUCTION; INTERMEDIATE; ASYMMETRIC ORGANOCATALYSIS; aminocatalysis; DIENAMINE CATALYSIS; NITROALKENES
• ISSN: 0947-6539; 1521-3765
• DOI: 10.1002/chem.201403505

The organocatalytic enantioselective syntheses of functionalized hydroisochromenes and chromenes by trienamine‐mediated [4+2]‐cycloaddition/nucleophilic ring‐closing and iminium‐ion/aminal‐mediated oxa‐Michael/Michael/nucleophilic ring‐closing with 2‐nitroallylic alcohols are presented. The corresponding cycloadducts, with up to five stereocenters, are formed in good yield and excellent enantioselectivities. The synthetic applications of the obtained products have been demonstrated. High five! The organocatalytic enantioselective syntheses of functionalized hydroisochromenes and chromenes by trienamine‐mediated [4+2]‐cycloaddition/nucleophilic ring closing and iminium‐ion/aminal‐mediated oxa‐Michael/Michael/nucleophilic ring closing with 2‐nitroallylic alcohols are presented. The corresponding cycloadducts, with up to five stereocenters, are formed in good yield and excellent enantioselectivities.