Convenient synthesis of enantiopure (R-) and (S-)-3-fluoro-3-aminomethylpyrrolidines

Yarmolchuk, Vladimir S.; Mykhalchuk, Vladimir L.; Mykhailiuk, Pavel K.

doi:10.1016/j.tet.2014.03.002

Cited by 13 publications

(7 citation statements)

References 27 publications

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“…30 The newly established method uses a nucleophilic alkyl phosphine (tri-n-butylphosphine) and lower reaction temperatures to access 2H-indazoles selectively from commercially available reagents under milder reaction conditions. 36 2.3.2 Enantioselective reactions. The scope of the method was demonstrated by the preparation of over 40 structurally diverse 2H-indazole examples.…”

Section: Selectivity In Heterocycle Formationmentioning

confidence: 99%

Modern advances in heterocyclic chemistry in drug discovery

et al. 2016

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New advances in synthetic methodologies that allow rapid access to a wide variety of functionalized heterocyclic compounds are of critical importance to the medicinal chemist as it provides the ability to expand the available drug-like chemical space and drive more efficient delivery of drug discovery programs. Furthermore, the development of robust synthetic routes that can readily generate bulk quantities of a desired compound help to accelerate the drug development process. While established synthetic methodologies are commonly utilized during the course of a drug discovery program, the development of innovative heterocyclic syntheses that allow for different bond forming strategies are having a significant impact in the pharmaceutical industry. This review will focus on recent applications of new methodologies in C-H activation, photoredox chemistry, borrowing hydrogen catalysis, multicomponent reactions, regio- and stereoselective syntheses, as well as other new, innovative general syntheses for the formation and functionalization of heterocycles that have helped drive project delivery. Additionally, the importance and value of collaborations between industry and academia in shaping the development of innovative synthetic approaches to functionalized heterocycles that are of greatest interest to the pharmaceutical industry will be highlighted.

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Section: Selectivity In Heterocycle Formationmentioning

confidence: 99%

Modern advances in heterocyclic chemistry in drug discovery

et al. 2016

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“…TFA (trifluoroacetic acid), room temp. }, which was originally developed by Achiwa and coworkers, and has been widely used by us and others in recent years, could be used for a reaction with the parent commercially available vinyl sulfonyl fluoride 1a (Scheme , R 1 = R 2 = H). We found that under these typical conditions, the target adduct 3a was obtained in 75 % yield (Table ).…”

Section: Resultsmentioning

confidence: 99%

[3+2] Cycloaddition of an Azomethyne Ylide and Vinyl Sulfonyl Fluorides ― an Approach to Pyrrolidine‐3‐sulfonyl Fluorides

et al. 2018

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“…Next, we changed the hydrogen substituent to a fluorine atom while keeping the same EWG (CO 2 Alk), and again varied the cyclic ketones (alkenes 9 – 12 ). Fluorinated pyrrolidines 9a – 12a were obtained in excellent yields of 71–91 %.…”

Section: Resultsmentioning

confidence: 99%