Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 85, Issue 8, Pages 5203-5219Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.9b03164
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Funding
- National Natural Science Foundation of China [21762013]
- Project of Guizhou Province [Qian Ke He Ping Tai Ren Cai [2017] 5726, Qian Jiao He KY Zi [2016] 133]
- Doctoral Research Funds of Guizhou Normal University (2015)
- Innovation and Entrepreneurship Project of Guizhou Province for Undergraduates [201710663066]
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A novel Michael/alkylation cascade reaction of N-unprotected 3-bromooxindoles with alpha,beta-unsaturated acyl phosphonates using DABCO as a robust catalyst followed by the derivatization of the acyl phosphonate intermediates in situ has been developed. This scenario enables rapid access to a diverse set of highly functionalized spirocyclopropyl oxindoles in moderate yields with good to excellent diastereoselectivities, which are analogues of a high active non-nucleoside reverse transcriptase inhibitor against HIV-1. The synthetic potential of this tactic has been highlighted by a gram-scale reaction and Suzuki cross-coupling reactions of the product. Moreover, the reaction mechanism has been tentatively elucidated by control experiments and dynamic high-resolution mass spectrometry studies, which indicates that the Michael/alkylation cascade reaction involves DABCO-derived alpha-substituted ammonium ylides.
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