Journal
ORGANIC LETTERS
Volume 23, Issue 24, Pages 9376-9381Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c03419
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Funding
- Czech Science Foundation [20-29336S]
- Charles University program START [CZ.02.2.69/0.0/0.0/19_0 73/0016935 (START/SCI/084)]
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The study presents a versatile method for the synthesis of chiral 2H-1,4-benzoxazines using chiral phosphoric acid catalysis, achieving high yields and enantioselectivity under mild conditions. This strategy expands on traditional methods and provides access to key intermediates for therapeutic candidates, such as prostaglandin D2 receptor antagonists and MI positive allosteric modulator (PAM) compound VU0486846.
Herein, we describe a versatile transition metal/oxidant free synthesis of the chiral 2H-1,4-benzoxazines through chiral phosphoric acid (CPA) catalyzed enantioselective desym-metrization 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 MI positive allosteric modulator (PAM) compound VU0486846.
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