Hemiaminals as substrates for sulfur ylides: direct asymmetric syntheses of functionalised pyrrolidines and piperidines.
نویسندگان
چکیده
Phenyl stabilised chiral sulfur ylides react with five-membered-ring hemiaminals to give functionalised pyrrolidines directly with high enantioselectivity. The reaction can be diverted to give piperidines instead by isolation of the intermediate epoxide and treatment with TMSOTf.
منابع مشابه
Synthesis of nitrogenated heterocycles by asymmetric transfer hydrogenation of N-(tert-butylsulfinyl)haloimines.
Highly optically enriched, protected, nitrogenated heterocycles with different ring sizes have been synthesized by a very efficient methodology consisting of the asymmetric transfer hydrogenation of N-(tert-butylsulfinyl)haloimines followed by treatment with a base to promote an intramolecular nucleophilic substitution process. N-protected aziridines, pyrrolidines, piperidines, and azepanes bea...
متن کاملAsymmetric Synthesis of New Diastereomerically Pure Spiro Oxindolopyrrolizidines and Oxindolopyrrolidines via Cycloaddition Reactions of Azomethine Ylides and Menthol-Drived Trans-Cinnamic
Chiral pyrrolidines and pyrrolizidines with spirooxindole ring systems are the central skeletons for numerous alkaloids and pharmacologically important compounds. Gelesmine, pseudotabersonine, formosanine, isoformosanine, morroniside and mitraphylline are some of the alkaloids containing spirooxindole ring systems. Derivatives of spirooxindole find very wide biological applications as anti micr...
متن کاملAsymmetric Synthesis of New Diastereomerically Pure Spiro Oxindolopyrrolizidines and Oxindolopyrrolidines via Cycloaddition Reactions of Azomethine Ylides and Menthol-Drived Trans-Cinnamic
Chiral pyrrolidines and pyrrolizidines with spirooxindole ring systems are the central skeletons for numerous alkaloids and pharmacologically important compounds. Gelesmine, pseudotabersonine, formosanine, isoformosanine, morroniside and mitraphylline are some of the alkaloids containing spirooxindole ring systems. Derivatives of spirooxindole find very wide biological applications as anti micr...
متن کاملRing expansion of vinylaziridines through the strain-release pericyclic reaction: recent developments and applications.
Recent syntheses of azetidines, pyrrolidines, piperidines and azepines through cycloaddition or sigmatropic rearrangements of vinylaziridines are described. Applications to natural product synthesis and mechanistic investigations are also summarized.
متن کاملOpportunities and challenges for direct C–H functionalization of piperazines
Piperazine ranks within the top three most utilized N-heterocyclic moieties in FDA-approved small-molecule pharmaceuticals. Herein we summarize the current synthetic methods available to perform C-H functionalization on piperazines in order to lend structural diversity to this privileged drug scaffold. Multiple approaches such as those involving α-lithiation trapping, transition-metal-catalyzed...
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید
ثبت ناماگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید
ورودعنوان ژورنال:
- Chemical communications
دوره 20 شماره
صفحات -
تاریخ انتشار 2006