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Asymmetric Synthesis of Polyfunctionalized Mono‐, Bi‐, and Tricyclic Carbon Frameworks via Organocatalytic Domino Reactions
Author(s) -
Enders Dieter,
Hüttl Matthias R. M.,
Raabe Gerhard,
Bats Jan W.
Publication year - 2008
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200700396
Subject(s) - chemistry , cascade reaction , domino , intramolecular force , stereoselectivity , organocatalysis , enantioselective synthesis , tricyclic , cyclohexene , cascade , combinatorial chemistry , bicyclic molecule , organic chemistry , catalysis , stereochemistry , chromatography
An asymmetric organocatalytic multi‐component domino reaction is used as a key process for the stereoselective synthesis of polysubstituted mono‐ and bicyclic cyclohexene‐carbaldehydes. Furthermore, the extension of the domino reaction and further synthetic transformations of the cascade products were investigated. The combination of the three‐step cascade with an intramolecular Diels–Alder reaction opens up an entry to tricyclic decahydroacenaphthylene and decahydrophenalene skeletons, which are valuable characteristic carbon cores of natural products.