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1.
J Org Chem ; 88(24): 17024-17036, 2023 Dec 15.
Article in English | MEDLINE | ID: mdl-37987742

ABSTRACT

Herein, we present a highly enantioselective desymmetrization of 3-substituted oxetanes enabled by a confined chiral phosphoric acid. This metal-free process allows effective access to chiral seven-membered 1,4-benzoxazepines with a high degree of enantiocontrol, under mild reaction conditions. The developed synthetic strategy tolerates a broad substrate scope and demonstrates its synthetic utility in various enantioselective product transformations, thus proving its effectiveness in diverse scenarios.

2.
Org Lett ; 25(29): 5520-5524, 2023 Jul 28.
Article in English | MEDLINE | ID: mdl-37462268

ABSTRACT

A photomediated protocol giving facile access to substituted ß-lactam and ß-lactones is presented. The method realizes, for the first time, the use of the Zimmerman-O'Connell-Griffin (ZOG) rearrangement in [2 + 2] cycloaddition. Products are obtained in high yield with excellent diastereoselectivity under visible light irradiation and under mild reaction conditions.

3.
J Org Chem ; 86(24): 18139-18155, 2021 12 17.
Article in English | MEDLINE | ID: mdl-34851113

ABSTRACT

The atom-economic method for the preparation of novel bispirocyclic compounds containing three fused heterocyclic scaffolds privileged in drug discovery was developed by using a chiral amine-squaramide Mannich reaction and Au(I)-catalyzed hydroamination. The developed synthetic strategy performed either stepwise or as a one-pot process allows the formation of chiral bispirocyclic [oxindole-pyrrolidine-pyrazolones] in high yields (up to 75%) with excellent enantioselectivities (up to 99%).


Subject(s)
Pyrazolones , Catalysis , Molecular Structure , Oxindoles , Pyrrolidines , Stereoisomerism
4.
Org Lett ; 23(24): 9376-9381, 2021 12 17.
Article in English | MEDLINE | ID: mdl-34817183

ABSTRACT

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.

5.
Beilstein J Org Chem ; 17: 2433-2440, 2021.
Article in English | MEDLINE | ID: mdl-34621405

ABSTRACT

Here we present an enantioselective aminalization of aldehydes catalyzed by Brønsted acids based on pentacarboxycyclopentadienes (PCCPs). The cyclization reaction using readily available anthranilamides as building blocks provides access to valuable 2,3-dihydroquinazolinones containing one stereogenic carbon center with good enantioselectivity (ee up to 80%) and excellent yields (up to 97%).

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