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Direct Access to Multifunctionalized Norcamphor Scaffolds by Asymmetric Organocatalytic Diels–Alder Reactions
Author(s) -
Mose Rasmus,
Jensen Magnus E.,
Preegel Gert,
Jørgensen Karl Anker
Publication year - 2015
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201507348
Subject(s) - stereocenter , chemistry , stereoselectivity , amide , cyclopentenone , organic chemistry , stereochemistry , enantioselective synthesis , catalysis
A general organocatalytic cross‐dienamine activation strategy to produce chiral multifunctionalized norcamphor compounds having a large diversity in substitution pattern is presented. The strategy is based on a Diels–Alder reaction of an amino‐activated cyclopentenone reacting with most common classes of electron‐deficient olefins, such as nitro‐, ester‐, amide‐, and cyano‐substituted olefins, chalcones, conjugated malononitriles, CF 3 ‐substituted enones, and fumarates. The corresponding norcamphor derivatives are formed in good yield, excellent enantioselectivities, and with complete diastereoselectivity. Furthermore, it is demonstrated that quaternary stereocenters and spiro norcamphor compounds can be formed with high stereoselectivity. The present development provides a simple, direct, and efficient approach for the preparation of important norcamphor scaffolds.