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Catalytic Enantioselective Formal Hetero‐Diels–Alder Reactions of Enones with Isatins to Give Spirooxindole Tetrahydropyranones
Author(s) -
Cui HaiLei,
Tanaka Fujie
Publication year - 2013
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.201300595
Subject(s) - enantioselective synthesis , catalysis , enamine , chemistry , diels–alder reaction , organic chemistry , organocatalysis , combinatorial chemistry
Organocatalytic formal hetero‐Diels–Alder reactions of enones with isatins, which gave highly enantiomerically enriched functionalized spirooxindole tetrahydropyranones via an enamine‐based mechanism, were developed. The catalyst systems were identified by a screen of combinations of amines, acids, and additives. With the identified catalyst systems, various spirooxindole tetrahydropyranones were synthesized in high yields with high diastereo‐ and enantioselectivities (see scheme).