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Chiral phosphoric acid-catalyzed enantioselective construction of structurally diverse benzothiazolopyrimidines

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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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
DOI: 10.1039/c8sc05581e

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