Journal
ACS COMBINATORIAL SCIENCE
Volume 16, Issue 6, Pages 293-302Publisher
AMER CHEMICAL SOC
DOI: 10.1021/co5000163
Keywords
N-sulfonyl iminiums; polymer-supported; stereoselective; tetrahydrobenzopyrazinothiadiazinone; sp3 carbon
Funding
- Department of Chemistry and Biochemistry at the University of Notre Dame [P207/12/0473]
- Czech Science Foundation (GACR)
- European Social Fund [CZ.1.07/2.3.00/20.0009]
- Operational Programme Research and Development for Innovations [CZ.1.05/2.1.00/01.0030]
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The stereoselective synthesis of 1,2,11,11a-tetrahydrobenzo [e]pyrazino [1,2-b] [1,2,4] thiadiazin-3 (4H)-one 6,6-dioxides on a solid support via tandem N-sulfonyl iminium ion cydization, followed by nucleophilic addition is reported. The synthesis proceeded with full control of stereoselectivity at the newly formed asymmetric carbon, under mild conditions, and using commercially available building blocks. The synthetic route provided high-purity crude products.
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