Jackson Zhu April 14th, 2017 Olson Group Meeting

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Presentation transcript:

Jackson Zhu April 14th, 2017 Olson Group Meeting Cascade reactions Jackson Zhu April 14th, 2017 Olson Group Meeting

Overview Cascade reaction = domino reaction = tandem reaction “chemical process that comprises at least two consecutive reactions such that each subsequent reaction occurs only in virtue of the chemical functionality formed in the previous step” - Wikipedia (Tietze, L. F.; Beifuss, U. Angew. Chemie Int. Ed. 1993, 32, 131–163.) * Nucleophilic/electrophilic cascades * Pericyclic cascades Radical, organocatalytic, transition-metal catalyzed cascades also exist but not emphasized today 

Indoles from pd catalyzed cascade 68% overall ~88% per step J. M. Knapp, J. S. Zhu, D. J. Tantillo, M. J. Kurth, Angewandte Chemie International Edition 2012, 51, 10588-10591.

Quinazolinotriazolobenzodiazepines 70% overall ~84% per step K. G. Guggenheim, H. Toru, M. J. Kurth, Org. Lett. 2012, 14, 3732.

Nitrile cascade 70% overall ~84% per step H. H. Nguyen, J. C. Fettinger, M. J. Haddadin, M. J. Kurth, Tetrahedron Lett. 2015, 56, 5429-5433.

Nitrile cascade 37% overall ~71% per step 54% overall ~81% per step A. L. Bagdasarian, H. H. Nguyen, T. A. Palazzo, J. C. Fettinger, M. J. Haddadin, M. J. Kurth, J. Org. Chem. 2016, 81, 3924-3928.

Davis-Beirut cascade 77% overall ~95% per step K. M. Farber, M. J. Haddadin, M. J. Kurth, J. Org. Chem. 2014, 79, 6939.

Heliotropamide 76% overall ~“87%” per step or 93% per “step” A. Younai, G. F. Chin, J. T. Shaw, J. Org. Chem. 2010, 75, 8333-8336.

Clerobungin A 40% overall ~63% per step J. Mease, K. P. Reber, J. Org. Chem. 2016, 81, 12006-12011.

Indoloquinolizidines 90% overall ~95% per step H. Fang, X. Wu, L. Nie, X. Dai, J. Chen, W. Cao, G. Zhao, Org. Lett. 2010, 12, 5366-5369.

Furo[3,2-c]pyridinones 85% overall ~95% per step F. Liang, S. Lin, Y. Wei, J. Am. Chem. Soc. 2011, 133, 1781-1783.

Taiwaniaquinol B 70% overall ~91% per step E. Fillion, D. Fishlock, J. Am. Chem. Soc. 2005, 127, 13144-13145.

Daphyniphylum D. J. Tantillo, Org. Lett. 2016, 18, 4482-4484.

Nitroso Acetals 81% overall ~90% per step G. S. Creech, O. Kwon, J. Am. Chem. Soc. 2010, 132, 8876.

En route to aminocyclohexanes 68% 79% S. E. Denmark, A. Stolle, J. A. Dixon, V. Guagnano, J. Am. Chem. Soc. 1995, 117, 2100-2101.

2,3-Benzodiazepines 70% overall ~89% per step Y. Matsuya, N. Ohsawa, H. Nemoto, J. Am. Chem. Soc. 2006, 128, 13072-13073.

vindorosine 87% overall ~95% per step G. I. Elliott, J. R. Fuchs, B. S. Blagg, H. Ishikawa, H. Tao, Z.-Q. Yuan, D. L. Boger, J. Am. Chem. Soc. 2006, 128, 10589-10595.

decalins Up to 91% overall ~97% per step E. L. Sauer, L. Barriault, J. Am. Chem. Soc. 2004, 126, 8569-8575.

benzosimuline 70% overall ~84% per step M. J. Riveira, A. La-Venia, M. P. Mischne, J. Org. Chem. 2016, 81, 7977-7983.

Endiandric acid b methyl ester 23% overall ~69% per step K. Nicolaou, N. Petasis, R. Zipkin, J. Am. Chem. Soc. 1982, 104, 5560-5562.

Hirsutellone B 50% overall ~79% per step K. P. Reber, S. D. Tilley, C. A. Carson, E. J. Sorensen, J. Org. Chem. 2013, 78, 9584.

Zincke Aldehyde R. S. Paton, S. E. Steinhardt, C. D. Vanderwal, K. Houk, J. Am. Chem. Soc. 2011, 133, 3895-3905.

Furanodendralenes T. Fallon, A. C. Willis, M. N. Paddon-Row, M. S. Sherburn, J. Org. Chem. 2014, 79, 3185-3193.

notable references K. Nicolaou, D. J. Edmonds, P. G. Bulger, Angew. Chem. Int. Ed. 2006, 45, 7134-7186. L. F. Tietze, Chem. Rev. 1996, 96, 115-136.