| Full text | |
| Author(s): |
Momo, Patricia B.
;
Mizobuchi, Eduardo F.
;
Echemendia, Radell
;
Baddeley, Isabel
;
Grayson, Matthew N.
;
Burtoloso, Antonio C. B.
Total Authors: 6
|
| Document type: | Journal article |
| Source: | Journal of Organic Chemistry; v. 87, n. 5, p. 9-pg., 2022-03-04. |
| Abstract | |
Enantioselective sulfa-Michael additions to alpha,beta-unsaturated diazocarbonyl compounds have been developed. Quinine-derived squaramide was found to be the best catalyst to promote C-S bond formation in a highly stereoselective fashion for alkyl and aryl thiols. The easy-to-follow protocol allowed the preparation of 22 examples in enantiomeric ratios up to 97:3 and reaction yields up to 94%. The mechanism and origins of enantioselectivity were determined through density functional theory (DFT) calculations. (AU) | |
| FAPESP's process: | 19/12300-5 - Synthesis of butenolides and butyrolactams from sulfur ylides and diazocompounds |
| Grantee: | Radell Echemendía Pérez |
| Support Opportunities: | Scholarships in Brazil - Post-Doctoral |
| FAPESP's process: | 20/07147-0 - Enantioselective alpha-heterofunctionalization of carbonyl compounds using sulfoxonium ylides |
| Grantee: | Antonio Carlos Bender Burtoloso |
| Support Opportunities: | Regular Research Grants |
| FAPESP's process: | 17/23329-9 - Synthesis of substituted cyclopentanes and long chain polyols from abundant chemical platforms derived from biomass |
| Grantee: | Antonio Carlos Bender Burtoloso |
| Support Opportunities: | Regular Research Grants |
| FAPESP's process: | 18/02920-3 - Thia-Michael additions and insertion reactions in a,b-unsaturated sulfur ylides |
| Grantee: | Eduardo Falcão Mizobuchi |
| Support Opportunities: | Scholarships in Brazil - Scientific Initiation |
| FAPESP's process: | 15/22003-7 - Asymmetric Aza-Michael Addition from unsaturated diazoketones. |
| Grantee: | Patrícia Betoni Momo |
| Support Opportunities: | Scholarships in Brazil - Post-Doctoral |