Enantioselective Fluorination Mediated by N-Fluoroammonium Salts of Cinchona Alkaloids: First Enantioselective Synthesis of BMS-204352 (MaxiPost)
- 13 February 2003
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 68 (6) , 2494-2497
- https://doi.org/10.1021/jo026792s
Abstract
We have employed a cinchona alkaloid/Selectfluor-mediated enantioselective fluorination of the oxindole 2 to achieve the first enantioslective synthesis of BMS-204352 (MaxiPost, S -1), an effective opener of maxi-K channels. Fluorination occurred to produce S -1 with 84% ee using the bis-cinchona alkaloid (DHQ)2AQN. Recrystallization produced enantiomerically pure (>99% ee) product. Quinidine-mediated fluorination of 2 gave the (R)-antipode of 1 with 68% ee.Keywords
This publication has 15 references indexed in Scilit:
- The Mechanism of Catalytic Enantioselective Fluorination: Computational and Experimental StudiesAngewandte Chemie International Edition in English, 2002
- Synthesis and Structure−Activity Relationships of 3-Aryloxindoles: A New Class of Calcium-Dependent, Large Conductance Potassium (Maxi-K) Channel Openers with Neuroprotective PropertiesJournal of Medicinal Chemistry, 2002
- Synthesis of Fluorogypsetin and Fluorobrevianamide E by a Novel Fluorination–Cyclization of cyclo‐L‐Trp‐L‐AAsAngewandte Chemie International Edition in English, 2001
- Targeting acute ischemic stroke with a calcium-sensitive opener of maxi-K potassium channelsNature Medicine, 2001
- N-Fluorocinchonidinium tetrafluoroborate F-CD-BF4: purification and structure elucidation of this novel enantioselective electrophilic fluorinating agentTetrahedron Letters, 2001
- Catalytic Enantioselective Fluorination ofβ-KetoestersPublished by Wiley ,2000
- Design, Synthesis, and Evaluation of a Novel Class of Enantioselective Electrophilic Fluorinating Agents: N-Fluoro Ammonium Salts of cinchona Alkaloids (F-CA-BF4)Organic Letters, 2000
- Enantioselective introduction of fluoride into organic compoundsJournal of Fluorine Chemistry, 2000
- A Novel and Efficient Synthesis of 3-Fluorooxindoles from Indoles Mediated by SelectfluorOrganic Letters, 2000
- New fluorinating reagents - I. The first enantioselective fluorination reactionTetrahedron Letters, 1988