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(Reference retrieved automatically from Web of Science through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

Cooperative copper-squaramide catalysis for the enantioselective N-H insertion reaction with sulfoxonium ylides

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Furniel, Lucas G. [1] ; Echemendia, Radell [1] ; Burtoloso, Antonio C. B. [1]
Total Authors: 3
[1] Univ Sao Paulo, Sao Carlos Inst Chem, BR-13560970 Sao Carlos, SP - Brazil
Total Affiliations: 1
Document type: Journal article
Source: CHEMICAL SCIENCE; v. 12, n. 21, p. 7453-7459, JUN 7 2021.
Web of Science Citations: 0

The first examples of a highly efficient and enantioselective carbene-mediated insertion reaction, from a sulfur ylide, are described. By way of a catalytic asymmetric insertion reaction into N-H bonds from carbonyl sulfoxonium ylides and anilines, using a copper-bifunctional squaramide cooperative catalysis approach, thirty-seven alpha-arylglycine esters were synthesized in enantiomeric ratios up to 92 : 8 (99 : 1 after a single recrystallization) and reaction yields ranging between 49-96%. Furthermore, the protocol benefits from quick reaction times and is conducted in a straightforward manner. (AU)

FAPESP's process: 18/17800-3 - New methodologies using sulfur ylides for the enantioselective alpha-Heterofunctionalization of carbonyl compounds
Grantee:Lucas Giani Furniel
Support type: Scholarships in Brazil - Doctorate (Direct)
FAPESP's process: 20/07147-0 - Enantioselective alpha-heterofunctionalization of carbonyl compounds using sulfoxonium ylides
Grantee:Antonio Carlos Bender Burtoloso
Support type: Regular Research Grants
FAPESP's process: 19/12300-5 - Synthesis of butenolides and butyrolactams from sulfur ylides and diazocompounds
Grantee:Radell Echemendía Pérez
Support type: Scholarships in Brazil - Post-Doctorate