Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 76, Issue 21, Pages 8869-8878Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo201596p
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Funding
- National Natural Science Foundation of China [20872041]
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By combining the copper(II)-catalyzed asymmetric Henry reaction of o-alkynylbenzaldehydes with subsequent gold(I)-catalyzed cycloisomerization, optically active 1H-isochromenes and 1,3-dihydroisobenzofurans were successfully synthesized in good overall yields with good to excellent enantioselectivities (up to 98%). Various substrates were investigated, and a correlation between the regioselectivity and electronic nature of the substrates was studied. The substrates with electrodonating groups at the alkynyl moiety preferred a 6-endo-dig manner to generated 1H-isochromenes 3 as main products (up to >30:1) while the ones with electron-withdrawing groups were inclined to undergo 5-exo-dig c-yclization to form I,3-dihydroisobenzofurans 4 (up to 1:5).
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