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Forlagets udgivne version
Organocatalytic enantioselective 1,3-dipolar [6+4] cycloadditions of pyrylium ion intermediates with fulvenes promoted by a chiral primary amine catalyst have been developed to proceed in moderate to good yields and high enantioselectivities. The resultant chiral bicyclo[6.3.0]undecane scaffold containing a transannular bridging ether is densely functionalised providing a rigid scaffold for further manipulations. Computational studies give important insights into the role of the primary amine catalyst. Analysis of the reaction shows that the catalytic reaction proceeds in a step-wise manner and rationalises the stereochemical outcome of the reaction. Several stereoselective complexity-generating transformations, facilitated by the diverse functional groups and transannular bridge, are presented, highlighting the versatility of the core towards a number of the cyclooctanoid natural products.
Originalsprog | Engelsk |
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Tidsskrift | Chemistry - A European Journal |
Vol/bind | 26 |
Nummer | 50 |
Sider (fra-til) | 11417-11422 |
Antal sider | 6 |
ISSN | 0947-6539 |
DOI | |
Status | Udgivet - sep. 2020 |
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