Abstract
The first examples of asymmetric Tamura cycloaddition reactions involving singly activated alkenes are reported. Homophthalic anhydride reacts with α-methyl nitrosytrenes in the presence of an alkaloid-based catalyst to generate fused bicyclic aromatic ketone products with three new stereocentres (which are susceptible to subsequent equilibration) in 12-99% ee. An unusual equilibration process which occurs in methanolic medium in the absence of a recognisable base via proton transfer at the α-carbon of an ester was investigated experimentally and computationally.
Original language | English |
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Pages (from-to) | 1463-1474 |
Number of pages | 12 |
Journal | Organic and Biomolecular Chemistry |
Volume | 15 |
Issue number | 6 |
Early online date | 23 Jan 2017 |
DOIs | |
Publication status | Published - 14 Feb 2017 |