Enantioselective Synthesis of Isatin‐Derived α‐(Trifluoromethyl)imine Derivatives: Phosphine‐Catalyzed γ‐Addition of α‐(Trifluoromethyl)imines and Allenoates. Issue 11 (24th March 2017)

• Record Type: Journal Article
• Authors: Gao, Yu‐Ning; Shi, Min
• Is Part Of: European journal of organic chemistry. Issue 11(2017)
• Page Start: 1552
• Page End: 1560
• Publication Date: 2017-03-24
• Subjects: α‐(Trifluoromethyl)imines -- γ‐Addition reactions -- Asymmetric catalysis -- Phosphanes -- Chirality; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201700048
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : 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. Abstract : 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.