Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 15, Issue 25, Pages 5298-5307Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c7ob01034f
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Funding
- NSFC [21372256, 21572264]
- National Science Foundation for Fostering Talents in Basic Research of China [J1210064]
- opening foundation of the Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University [2014GDGP0103]
- National S&T Pillar Program of China [2015BAK45B01]
- National Key R&D Program of China [2016YFD0200205-4]
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The phosphine-catalyzed [3 + 2] annulation reaction of ynones and barbiturate-derived alkenes has been developed with the assistance of a weak acid, giving functionalized spirobarbiturate-cyclopentanones in moderate to excellent yields with excellent E/Z stereoselectivity. An unprecedented [4 + 2] annulation of ynones with barbiturate-derived alkenes was also achieved in the presence of a phosphine catalyst and an inorganic base, affording biologically interesting 1,5-dihydro-2H-pyrano[2,3-d]pyrimidine-2,4(3H)-dione derivatives. An asymmetric variant of the [3 + 2] annulation reaction has been explored and a moderate enantioselectivity was obtained when a bifunctional chiral phosphine was used as a chiral catalyst. A plausible mechanism was proposed to illuminate two different reaction pathways.
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