Journal
ACS CATALYSIS
Volume 6, Issue 1, Pages 151-154Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.5b02182
Keywords
asymmetric synthesis; chiral anion; cyclization; fluorination; phase-transfer catalyst
Categories
Funding
- NIHGMS [R01 GM104534]
- Asubio Pharma
- Mitsubishi Tanabe Pharma Corporation
- NSERC (Canada)
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Stereoselective synthesis of two fluorine-bearing drug-like scaffolds, dihydroquinazolone and benzooxazinone, has been accomplished through asymmetric fluorocyclization reactions initiated by the fluorination process. The reaction employs double axially chiral anionic phase-transfer catalysts to achieve high diastereo- and enantioselectivities, and a wide range of fluorine-containing dihydroquinazolones were obtained (>20:1 dr, up to 98% ee).
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