Enantioselective Synthesis of Isatin‐Derived α‐(Trifluoromethyl)imine Derivatives: Phosphine‐Catalyzed γ‐Addition of α‐(Trifluoromethyl)imines and Allenoates

We have described the first asymmetric umpolung γ‐addition reaction of isatin‐derived α‐(trifluoromethyl)imines and allenoates. A chiral multifunctional phosphine catalyst derived from an amino acid promotes this reaction very well under mild conditions to give a series of enantiomerically enriched...

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Bibliographic Details
Published in:European journal of organic chemistry 2017-03, Vol.2017 (11), p.1552-1560
Main Authors: Gao, Yu‐Ning, Shi, Min
Format: Article
Language:English
Subjects:
Asymmetric catalysis
Chirality
Phosphanes
α‐(Trifluoromethyl)imines
γ‐Addition reactions
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Summary:We have described the first asymmetric umpolung γ‐addition reaction of isatin‐derived α‐(trifluoromethyl)imines and allenoates. A chiral multifunctional phosphine catalyst derived from an amino acid promotes this reaction very well under mild conditions to give a series of enantiomerically enriched isatin‐derived α‐(trifluoromethyl)imine derivatives in high yields and with moderate to good enantioselectivities. An asymmetric umpolung γ‐addition reaction of isatin‐derived α‐(trifluoromethyl)imines and allenoates has been developed, giving enantiomerically enriched isatin‐derived α‐(trifluoromethyl)imine derivatives in high yields with moderate to good enantioselectivities.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201700048