Abstract
A short asymmetric synthesis of an all-syn and all-trans kainoid core is reported. The synthetic route relies on the application of a new asymmetric [3+2] annulation reaction followed by a conjugate addition reaction to install this kainoid's three stereocenters. A surprising intramolecular conjugate addition enabled by the chiral tert-butylsulfinyl group residing on the 3-pyrroline nitrogen atom surpassed its expected role as a steric spectator. Efforts to outcompete intramolecular 1,4-addition by further oxidizing the sulfoxide, or use of additives, and advancement of the all-syn addition product to the requisite kainoid common core are detailed.
Original language | English (US) |
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Pages (from-to) | 1041-1044 |
Number of pages | 4 |
Journal | Asian Journal of Organic Chemistry |
Volume | 8 |
Issue number | 7 |
DOIs | |
State | Published - Jul 2019 |
Externally published | Yes |
Keywords
- anionic cascade
- annulation
- asymmetry
- kainic acid
- sulfonamide
ASJC Scopus subject areas
- Organic Chemistry
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CCDC 1478415: Experimental Crystal Structure Determination
Chogii, I. (Contributor), Das, P. (Contributor) & Njardarson, J. T. (Contributor), Cambridge Crystallographic Data Centre, 2021
DOI: 10.5517/ccdc.csd.cc1lmdtf, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc1lmdtf&sid=DataCite
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