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Organocatalytic Cascade Reactions: Towards the Diversification of Hydroisochromenes and Chromenes through Two Different Activation Modes
Author(s) -
Cruz Cruz David,
Mose Rasmus,
Villegas Gómez Clarisa,
Torbensen Stine V.,
Larsen Martin S.,
Jørgensen Karl Anker
Publication year - 2014
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201403505
Subject(s) - stereocenter , nucleophile , cycloaddition , chemistry , aminal , iminium , enantioselective synthesis , michael reaction , organocatalysis , yield (engineering) , ring (chemistry) , nucleophilic addition , stereochemistry , combinatorial chemistry , organic chemistry , ion , catalysis , materials science , metallurgy
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.