Co-reporter:Kirill Tchabanenko, Colleen Sloan, Yves-Mael Bunetel and Philip Mullen
Organic & Biomolecular Chemistry 2012 vol. 10(Issue 21) pp:4215-4219
Publication Date(Web):19 Mar 2012
DOI:10.1039/C2OB07007C
Chiral enamides 5f–i were found to react with pyrylium ylides to give cycloadducts 6d–i in good yields with an excellent level of stereoselectivity. The chiral auxiliary was successfully removed on hydrogenolysis of compound 6f in continuous flow (H-Cube) resulting in the first asymmetric synthesis of complex amine 8.
Co-reporter:Kirill Tchabanenko, Peter McIntyre, John F. Malone
Tetrahedron Letters 2010 Volume 51(Issue 1) pp:86-88
Publication Date(Web):6 January 2010
DOI:10.1016/j.tetlet.2009.10.081
The tropolone subunit of the naturally occurring alkaloid rubrolone aglycon is synthesized via a short reaction sequence starting with a 1,3-dipolar cycloaddition of a pyrylium ylide and indenone, followed by enone oxidation, oxygen-bridge elimination and finally hydroxy group oxidation.
Co-reporter:Kirill Tchabanenko, Colleen Sloan, Yves-Mael Bunetel and Philip Mullen
Organic & Biomolecular Chemistry 2012 - vol. 10(Issue 21) pp:NaN4219-4219
Publication Date(Web):2012/03/19
DOI:10.1039/C2OB07007C
Chiral enamides 5f–i were found to react with pyrylium ylides to give cycloadducts 6d–i in good yields with an excellent level of stereoselectivity. The chiral auxiliary was successfully removed on hydrogenolysis of compound 6f in continuous flow (H-Cube) resulting in the first asymmetric synthesis of complex amine 8.
