Journal
ORGANIC LETTERS
Volume 19, Issue 12, Pages 3111-3114Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.7b01221
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Funding
- National Natural Science Foundation of China [21602023, 21572027, 21402150, 21672158]
- National University of Singapore [R-143-000-599-112]
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A phospbine-catalyzed novel enantioselective [4 -17]-arinulation reaction between allene ketones and 1-azadienes has been, developed, and tetrahydropyridines were obtained in good yields and with excellent enantioselectivities. Subsequent exposure of tetrahydropyridines to benzyne leads to a [2 + 2 ]-cyclization, creating optically enriched polycyclic pipericlines With a quaternary tereogeriic center and a cyclobutene moiety. The reported stepwise [4 +]/[2 + 2]-eyeloadditions represent a new approach to access enantiomerically enriched nitrogen-containing six-membered ring systems.
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