Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 83, Issue 2, Pages 614-623Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.7b02533
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Funding
- National Natural Science Foundation of China [21772069, 21702077]
- Natural Science Foundation of Jiangsu Province [BK20160003, BK20170227]
- Six Kinds of Talents Project of Jiangsu Province [SWYY-025]
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A catalytic asymmetric [4+2] cycloaddition of ortho-quinone methide imines in situ generated from oaminobenzyl alcohols with o-hydroxystyrenes has been established under the catalysis of chiral phosphoramide, which afforded chiral tetrahydroquinolines in moderate to good yields, good enantioselectivities, and excellent diastereoselectivities (up to 82% yield, 93:7 er, all >95:5 dr). In this catalytic asymmetric [4+2] cycloaddition, the hydrogen-bonding interaction between chiral phosphoramide and two substrates was proposed to play a crucial role in controlling the enantioselectivity. This reaction not only provides a useful approach for constructing chiral tetrahydroquinoline frameworks, but also demonstrates the great practicability of ortho-quinone methide imines in catalytic asymmetric cycloadditions.
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