Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 77, Issue 4, Pages 1961-1973Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo202553a
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Funding
- NSF [CHE-9726471]
- NIH [1F31GM089137]
- UC
- BMS
- CRIF [CHE-0840513]
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [0840513] Funding Source: National Science Foundation
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2-Vinylchromanes (1), 2-vinyl-1,4-benzodioxanes (2), and 2,3-dihydro-2-vinyl-2H-1,4-benzoxazines (3) can be prepared in high yields (90-98%) and excellent enantiomeric purities (87-98% ee) by [COP-OAc](2)-catalyzed cyclization of phenolic (E)-allylic trichloroacetimidate precursors. Deuterium-labeling and computational experiments are consistent with these cyclization reactions taking place by an anti-oxypalladation/syn-deoxypalladation mechanism. 2-Vinylchromanes can also be prepared in good yields and high enantiomeric purities from analogous (E)-allylic acetate precursors, which constitutes the first report that acetate is a competent leaving group in COP-catalyzed enantioselective S(N)2' substitution reactions.
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