Dearomative [4 + 3] cycloaddition of furans with vinyl-<i>N</i>-triftosylhydrazones by silver catalysis: stereoselective access to oxa-bridged seven-membered bicycles

نویسندگان

چکیده

A practical dearomative [4 + 3] cycloaddition of furans with vinylcarbenes to access oxa-bridged seven-membered carbocycles, complete and predictable stereoselectivity, is achieved by merging silver catalysis vinyl- N -triftosylhydrazones.

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

Six- and Seven-Membered 1-Oxa-4-Aza-2-Silacyclanes as Possible Correctors of Adaptational Mechanisms

The biological activity of eight 1-oxa-4-aza-2-silacyclanes with the OSiCH(2)N fragment including 6-membered 2-sila-5-morpholinones (1-3) and 4-acyl-2-silamorpholines (4-6)and previously unknown 7-membered derivatives of salicylic acid (7, 8) was studied. Compounds 1 and 3-6 show the certain antihypoxic action. Compounds 2 (40 mg/kg), 4 (20 mg/kg), 6 (40 mg/kg), 7 (20 mg/kg) and 8 (40 mg/kg) re...

متن کامل

[4 + 3] Cycloaddition of aromatic α,β-unsaturated aldehydes and ketones with epoxides: one-step approach to synthesize seven-membered oxacycles catalyzed by Lewis acid.

A novel intermolecular [4 + 3] cycloaddition method to construct 1,4-dioxide seven-membered oxacycles was developed. This one-step method was carried out in the presence of catalytic amount of (C(2)H(5))(2)OBF(3) under mild conditions. Seven-membered oxacycles and some natural compounds could be easily synthesized via this protocol. Control experiments were carried out and possible mechanism fo...

متن کامل

Highly Stereoselective Synthesis of Polycyclic Indoles through Rearrangement/[4+2] Cycloaddition under Sequential Catalysis

The indole moiety is a privileged structural motif in many biologically active and medicinally valuable molecules. Polycyclic frameworks lead to relatively rigid structures that could be expected to show substantial selectivity in their interactions with enzymes or receptors. Construction of polycyclic indoles usually requires multistep approaches. The preparation of polyfunctional indoles is t...

متن کامل

Correction: A novel Prins cascade process for the stereoselective synthesis of oxa-bicycles.

E- and Z-9-Methyldeca-3,8-dien-1-ols undergo smooth cyclization with aldehydes in the presence of 20 mol% AgSbF6 under extremely mild conditions to generate the corresponding oxa-bicycles in good yields with excellent selectivity. In fact, E-olefin affords the trans-product exclusively, whereas the Z-olefin gives the cis-product predominantly. In the case of E- or Z-8-methylnona-3,8-dien-1-ol, ...

متن کامل

Stereoelectronic Model To Explain Highly Stereoselective Reactions of Seven-Membered-Ring Oxocarbenium-Ion Intermediates.

Nucleophilic attack on seven-membered-ring oxocarbenium ions is generally highly stereoselective. The preferred mode of nucleophilic attack forms the product in a conformation that minimizes transannular interactions, thus leading to different stereoselectivity as compared to that of reactions involving six-membered-ring oxocarbenium ions.

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: Organic chemistry frontiers

سال: 2022

ISSN: ['2052-4110', '2052-4129']

DOI: https://doi.org/10.1039/d2qo00256f