Jarrige, Lucie; Glavač, Danijel; Levitre, Guillaume; Retailleau, Pascal; Bernadat, Guillaume; Neuville, Luc; Masson, Géraldine (2019) Chiral phosphoric acid-catalyzed enantioselective construction of structurally diverse benzothiazolopyrimidines. Chemical Science, 10 (13). pp. 3765-3769. ISSN 2041-6520
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Abstract
A highly efficient catalytic enantioselective [4+2] cycloaddition was developed between 2- benzothiazolimines and enecarbamates. A wide range of benzothiazolopyrimidines bearing three contiguous stereogenic centers was obtained in high to excellent yields and with excellent diastereo- and enantioselectivities (d.r. > 98 : 2 and up to >99% ee). Furthermore, this chiral phosphoric acid- catalyzed strategy was scalable and enabled access to a new class of optically pure Lewis base isothiourea derivatives.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | asymmetric organocatalysis ; chiral Brønsted acid ; benzothiazolopyrimidines ; Lewis base isothiourea derivatives ; homobenzotetramisole (HBTM) |
| Subjects: | NATURAL SCIENCES > Chemistry |
| Divisions: | Division of Organic Chemistry and Biochemistry |
| Depositing User: | Ivana Končić |
| Date Deposited: | 08 Feb 2022 09:42 |
| URI: | http://fulir.irb.hr/id/eprint/6972 |
| DOI: | 10.1039/c8sc05581e |
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