Catalytic Asymmetric (3 + 3) Cycloaddition of Oxyallyl Zwitterions with α-Diazomethylphosphonates
- 8 September 2021
- journal article
- research article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 23 (18), 7295-7300
- https://doi.org/10.1021/acs.orglett.1c02809
Abstract
The unique structure of oxyallyls represents a significant challenge for their catalytic asymmetric applications. Herein, an unprecedented chiral imidodiphosphoric acid-catalytic enantioselective (3 + 3) cycloaddition between oxyallyl zwitterions generated in situ from a-haloketones and alpha-diazomethylphosphonates was developed. Pharmaceutically interesting chiral pyridazine4(1H)-ones were obtained in up to 98% yields with excellent stereoselectivities (up to 99% ee, > 99:1 dr).Keywords
Funding Information
- Ministry of Education of the People's Republic of China (XDJK2019AA003)
- Natural Science Foundation of Chongqing (cstc2019jcyj-msxmX0414)
- National Natural Science Foundation of China (21472151)
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