Asymmetric Organocatalytic Synthesis of <i>aza</i> ?Spirocyclic Compounds from Isothiocyanates and Isocyanides

نویسندگان

چکیده

The spirocyclic motif is present in natural products, chiral ligands, and compounds of pharmacological interest. Isothiocyanates as well isocyanides bearing electron-withdrawing groups the ?-position can be deprotonated react formal dipoles on account presence a nucleophilic carbanion an electrophilic atom isothiocyanate or isocyanide functional groups. In last years number procedures involving [3+2] cycloaddition reaction isothiocyanates with cyclic exocyclic double bonds have been developed for enantioselective synthesis aza-spirocyclic compounds. Among them, organocatalysis has played predominant role development asymmetric versions these reactions. spirooxindoles by using this methodology received especial attention, although other scaffolds are available depending structure dipolarophiles dipoles.

برای دانلود باید عضویت طلایی داشته باشید

برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

منابع مشابه

synthesis of sulfides from alcohols and thiols in solvent-freeconditions and deoxygenation of sulfoxides

کاتالیست یک سنتز جدید برای تیواترها توصیف شده است. واکنش الکل ها با آریل، هتروآریل و آلکیل تیو ل ها درحضور 1،3،5- تری آزو- 2،4،6- تری فسفرین-2،2،4،4،6،6 هگزاکلراید ((tapc به عنوان یک کاتالیست موُثر، بازده های خوب تا عالی از تیواترها را حاصل می کند. علاوه براین، واکنش تحت شرایط بدون فلز و بدون حلال پیش می رود، بنابراین یک مکمل جالب برای روش های شناخته شده سنتز تیواترها ارائه می دهد. یک مکانیسم ا...

15 صفحه اول

Organocatalytic Asymmetric Synthesis and Use of Organoselenium Com- pounds Synthesis and Use of Organoselenium Compounds

In the last ten years organocatalysis has emerged as an efficient and sustainable strategy for the asymmetric synthesis of chiral molecules. Optically active intermediates for novel interesting transformations are generated under mild and operationally simple conditions when selenium-containing compounds are used as reaction partners. The peculiar reactivity of organoselenium compounds has been...

متن کامل

Organocatalytic activation of isocyanides: N-heterocyclic carbene-catalyzed enaminone synthesis from ketones.

The first example of the use of an N-heterocyclic carbene (NHC) as an organocatalyst for the activation of isocyanides was demonstrated. On the basis of previous reports on the interaction between NHCs and isocyanides, we developed a catalytic cycle involving transient imidoyl intermediate. The reaction of ketones with isocyanides produced the corresponding enaminones with high efficiency. Cont...

متن کامل

One-Pot Two-Step Organocatalytic Asymmetric Synthesis of Spirocyclic Piperidones via Wolff Rearrangement–Amidation–Michael–Hemiaminalization Sequence

A highly enantioselective organocatalytic Wolff rearrangement–amidation–Michael– hemiaminalization stepwise reaction is described involving a cyclic 2-diazo-1,3-diketone, primary amine and α,β-unsaturated aldehyde. Product stereocontrol can be achieved by adjusting the sequence of steps in this one-pot multicomponent reaction. This approach was used to synthesize various optically active spiroc...

متن کامل

ذخیره در منابع من


  با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید

ژورنال

عنوان ژورنال: European Journal of Organic Chemistry

سال: 2021

ISSN: ['1434-193X', '1099-0690']

DOI: https://doi.org/10.1002/ejoc.202100232