Enantioselective [2 + 2] cycloaddition of N-allenamides with cyclic N-sulfonylketimines: access to polysubstituted azetidines bearing quaternary stereocenters† †Electronic supplementary information (ESI) available: Experimental procedure, characterization data for all the new compounds, and chiral HPLC spectra for the products. CCDC 1495550. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c6sc05450a Click here for additional data file. Click here for additional data file.

نویسندگان

  • Ren-Rong Liu
  • Jiang-Ping Hu
  • Jian-Jun Hong
  • Chuan-Jun Lu
  • Jian-Rong Gao
  • Yi-Xia Jia
چکیده

A Ni(ClO4)2-catalyzed enantioselective [2 + 2] cycloaddition ofN-allenamides with cyclicN-sulfonylketimines was developed, which regioselectively occurred at the proximal C]C bonds of the N-allenamides. Broad substrate scope of N-allenamides and cyclic N-sulfonylketimines was observed. A range of fused polysubstituted azetidines bearing quaternary stereocenters were afforded in good yields and with excellent enantioselectivities (up to 99%).

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

ثبت نام

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

منابع مشابه

Gold(i)-catalyzed [2 + 2 + 2] cycloaddition of allenamides, alkenes and aldehydes: a straightforward approach to tetrahydropyrans† †Electronic supplementary information (ESI) available: Characterization data and experimental procedures. CCDC 1038447–1038449. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c5sc00295h Click here for additional data file. Click here for additional data file.

Centro Singular de Investigación en Qúım (CIQUS) and Departamento de Qúımica Compostela, C/ Jenaro de la Fuente s/n, E-mail: [email protected]; fernan Instituto de Qúımica Orgánica General (CS Spain † Electronic supplementary information and experimental procedures. CCDC crystallographic data in CIF or o 10.1039/c5sc00295h ‡ HF and IV equally contributed to this w Cite this: Chem. Sci....

متن کامل

Enantioselective Narasaka–Heck cyclizations: synthesis of tetrasubstituted nitrogen-bearing stereocenters† †Electronic supplementary information (ESI) available: Experimental procedures and characterisation data for all compounds are provided. CCDC 1438659 and 1438660. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c6sc04466b Click here for additional data file. Click here for additional data file.

School of Chemistry, University of Bristol, B bris.ac.uk AstraZeneca, Alderley Park, Maccleseld, C AstraZeneca, Pepparedsleden 1, Mölndal, 4 † Electronic supplementary information ( and characterisation data for all compou 1438660. For ESI and crystallographic dat DOI: 10.1039/c6sc04466b ‡ These authors contributed equally. § Author to whom correspondence shou structures of 3b and Pd[(Sa,S)-L-...

متن کامل

Enantioselective palladium(0)-catalyzed intramolecular cyclopropane functionalization: access to dihydroquinolones, dihydroisoquinolones and the BMS-791325 ring system† †Electronic supplementary information (ESI) available: Experimental procedures and characterization of all new compounds. CCDC 1401582. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c5sc01909e Click here for additional data file. Click here for additional data file.

Taddol-based phosphoramidite ligands enable enantioselective palladium(0)-catalyzed C–H arylation of cyclopropanes. The cyclized products are obtained in high yields and enantioselectivities. The reported method provides efficient access to a broad range of synthetically attractive cyclopropyl containing dihydroquinolones and dihydroisoquinolones as well as allows for an efficient enantioselect...

متن کامل

Enantioselective allylic alkylation of stereodefined polysubstituted copper enolates as an entry to acyclic quaternary carbon stereocentres† †Electronic supplementary information (ESI) available. CCDC 1488151. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c6sc03036j Click here for additional data file. Click here for additional data file.

Table of Contents General methods S1 Reagents and materials S2 General protocol for the preparation of starting chiral ynamides S3 General procedures for the allylation of stereodefined trisubstituted copper enolate S5 Optimization reactions S8 Products of the enantioselective allylic alkylation reaction S9 Cleavage of oxazolidinone moiety 4 S19 References S21 X-Ray crystallographic analysis da...

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

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

ثبت نام

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

عنوان ژورنال:

دوره 8  شماره 

صفحات  -

تاریخ انتشار 2017