Seminar: Polarity inversion of vinyl ketones and related conjugate acceptors. Access to nucleophiles and bases to enable reaction discovery (Professor David Lupton)

Thursday, 26 September 2019 - 3:00pm – Thursday, 26 September 2019 - 4:00pm  |  ChemSci M17

Abstract

In 1962 Price observed the formation of homoenolate intermediates when acrylonitrile is exposed to phosphine catalysts in the presence of alcohols.1 More recently, studies from our group, and others, have focused on reaction discovery through related species formed under NHC catalysis.2 In this presentation I will focus on our recent studies with this intermediate and related structures that have enabled discoveries in synthesis.3,4 This family of intermediates is extremely robust and can be deployed in a range of polar3 and none polar reaction designs.4

 

1. Takashina, N.; Price, C. C. J. Am. Chem. Soc. 1962, 84, 489–491

2. a) Chem. Soc. Rev. 2013, 42, 4906–4917; b) Chen, X.-Y., Ye, S. Org. Biomol. Chem. 2013, 11, 7991–7998

3. a) Nakano, Y.; Lupton, D. W. Angew. Chem. Int. Ed. 2016, 55, 3135–3139; b) Scott, L.; Nakano, Y.; Zhang, C.; Lupton, D. W. Angew. Chem. Int. Ed. 2018, 57, 10299-10303; c) Nguyen, X. B.; Nakano, Y.; Duggan, N. Scott, L.; Breugst, M.; Lupton, D. W. Angew. Chem. Int. Ed. 2019, 131, 11607 d) Fernando, J. E. M.; Nakano, Y.; Zhang, C.; Lupton, D. W. Angew. Chem. Int. Ed. 2019, 53, 2905; e) Bae, S.; Zhang, C.; Gillard, R. M.; Lupton, D. W. Angew. Chem. Int. Ed. 2019, DOI: 10.1002/anie.201907111.

4. Nguyen, X. B.; Cao, J.; Pitchumani, V.; Williamson, D. A.; Lupton, D. W. unpublished