Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 83, Issue 19, Pages 12207-12212Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.8b01565
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Funding
- National Institutes of Health [GM-087605]
- NSF [1S10RR023444, 1S10RR022442, CHE 0840438, CHE-0848460, 1S10OD011980]
- NATIONAL CENTER FOR RESEARCH RESOURCES [S10RR023444, S10RR022442] Funding Source: NIH RePORTER
- NATIONAL INSTITUTE OF GENERAL MEDICAL SCIENCES [R01GM087605] Funding Source: NIH RePORTER
- OFFICE OF THE DIRECTOR, NATIONAL INSTITUTES OF HEALTH [S10OD011980] Funding Source: NIH RePORTER
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A chiral oxazaborolidine combined with SnCl4 has been found to promote the dearomative spirocyclization of electron-rich benzyl allenyl ketones. The reaction outcome is sensitive to the nature of activating acid, which was rationalized using hard-soft acid-base (HSAB) theory. The spirocyclic product was obtained with up to 72% ee, which is the best result reported to date for these substrates. The formation of cross-conjugated or conjugated products is readily controlled by changing the oxygen protecting groups.
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