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Synthesis of new quinuclidine derivatives via Pd-mediated cross-coupling and cross-benzannulation reactions |
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| Authors: | Stefania Tötös Manfred Fild Ion Grosu |
| Institution: | a ‘Raluca-Ripan’ Institute for Research in Chemistry, ‘Babes-Bolyai’ University, 30 Fantanele str., 400294, Cluj-Napoca, Romania b Institut für Anorganische und Analytische Chemie der Technischen Universität, Hagenring 30, 38106 Braunschweig, Germany c Faculty of Chemistry and Chemical Engineering, ‘Babes-Bolyai’ University, 11 Arany Janos str., 400028, Cluj-Napoca, Romania |
| Abstract: | New functionalized quinuclidines were prepared via palladium-catalyzed addition reactions of terminal alkynes (donors) to internal alkynes (acceptors). The enantiopure terminal alkynes were derivatives of quincoridine and quincorine, two semi-natural Cinchona alkaloids. The processes exhibited high chemoselectivity and excellent diastereoselectivity, the E-enynes being obtained as single products in almost all cases. The synthesis of new tetra and pentasubstituted benzene derivatives in good yields by 2+2+2] benzannulation of the diynes, obtained by the palladium-catalyzed homodimerization of 10,11-didehydro quincoridine and 10,11-didehydro quincorine, with terminal alkynes and in fair yield by 4+2] benzannulation of an enyne derivative of 10,11-didehydro quincoridine with 2,4-hexane-diyne are reported. |
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