Enantioselective Desymmetrization of 3-Substituted Oxetanes: An Efficient Access to Chiral 3,4-Dihydro-2H-1,4-benzoxazines

0549868 - ÚOCHB 2022 RIV US eng J - Článek v odborném periodiku
Bhosale, V. A. - Nigríni, M. - Dračínský, Martin - Císařová, I. - Veselý, J.
Enantioselective Desymmetrization of 3-Substituted Oxetanes: An Efficient Access to Chiral 3,4-Dihydro-2H-1,4-benzoxazines.
Organic Letters. Roč. 23, č. 24 (2021), s. 9376-9381. ISSN 1523-7060. E-ISSN 1523-7052
Institucionální podpora: RVO:61388963
Klíčová slova: Enantioselective synthesis * phosphoric acid * organic catalysis
Obor OECD: Organic chemistry
Impakt faktor: 6.072, rok: 2021
Způsob publikování: Omezený přístup
https://doi.org/10.1021/acs.orglett.1c03419

Herein, we describe a versatile transition metal/oxidant free synthesis of the chiral 2H-1,4-benzoxazines through chiral phosphoric acid (CPA) catalyzed enantioselective desymmetrization of prochiral oxetanes (30 examples) in up to 99% yield and 99% enantioselectivity under mild reaction conditions. The reported strategy not only complements the conventional 2H-1,4-benzoxazine synthetic strategies but also provides access to key intermediates of therapeutic candidates, i.e., prostaglandin D2 receptor antagonist and M1 positive allosteric modulator (PAM) compound VU0486846.
Trvalý link: http://hdl.handle.net/11104/0325761


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