Journal
ACS CATALYSIS
Volume 7, Issue 10, Pages 6984-6989Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.7b02279
Keywords
Asymmetric catalysis; Chemoselectivity; Dearomatization; Enantioselectivity; Organocatalysis; Tryptophol
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Funding
- NSFC [21372002, 21232007]
- PAPD
- Natural Science Foundation of Jiangsu Province [BK20160003]
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Catalyst-controlled chemoselective and enantioselective reactions of tryptophols with isatin-derived imines were demonstrated. Under catalysis with a chiral phosphoric acid, diastereoselective and enantioselective dearomative cyclization occurred, while, in the presence of a chiral squaramide-tertiary amine, enantioselective addition occurred. Both reactions afforded 3-substituted 3-amino-oxindoles in generally good yields (up to 99%) and excellent stereoselectivities (up to >95:5 dr, 99:1 er).
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