Journal
ACS CATALYSIS
Volume 8, Issue 11, Pages 10234-10240Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.8b03410
Keywords
asymmetric catalysis; cyclization; enantioselectivity; metal catalysis; vinyl aziridine; para-quinone methide
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Funding
- NSFC [21772069, 21702077]
- Natural Science Foundation of Jiangsu Province [BK20160003, BK20170226]
- Six Kinds of Talents Project of Jiangsu Province [SWYY-025]
- Postgraduate Research and Practice Innovation Program of Jiangsu Province [KYCX18_2107]
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The development of (4 + 3) cyclizations of vinyl aziridines, especially catalytic asymmetric versions, is needed in organic synthesis. This report describes an iridium-catalyzed (4 + 3) cyclization of vinyl aziridines with paraquinone methide (p-QM) derivatives, and this reaction constructs a seven-membered benzoxazepine scaffold in moderate to high yields (40% to 96%) and considerable diastereoselectivities (70:30 dr to >95:5 dr). Moreover, the catalytic asymmetric version of this (4 + 3) cyclization is accomplished in the presence of a palladium catalyst and a chiral ligand, and this modification provides chiral benzoxazepine derivatives in generally moderate diastereoselectivities (73:27 dr to 91:9 dr) and high enantioselectivities (92:8 to 96:4 er). This approach delivers a scarcely reported catalytic enantioselective (4 + 3) cyclization of vinyl aziridines and offers a metal-catalyzed (4 + 3) cyclization of p-QM derivatives.
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