Literature DB >> 28808413

Diastereoselective Intramolecular Cyanoamidation with Alkenes.

Ashley M Dreis1, Sadie C Otte1, Matthew S Eastwood1, Elizabeth R Alonzi1, Jason T Brethorst1, Christopher J Douglas1.   

Abstract

Reported herein is a diastereoselective intramolecular alkene cyanoamidation, wherein high d.r. values are imparted by chiral directing groups. Lactams with an α-all-carbon quaternary stereocenter are readily synthesized, which may enable access to structures frequently found in biologically active molecules and natural products.

Entities:  

Keywords:  Bond Activation; Cyanoamidation; Diastereoselectivity; Homogeneous catalysis; Palladium

Year:  2016        PMID： 28808413      PMCID： PMC5553975          DOI： 10.1002/ejoc.201601283

Source DB:  PubMed          Journal:  European J Org Chem        ISSN： 1099-0690


  8 in total

1.  Intramolecular arylcyanation of alkenes catalyzed by nickel/AlMe2Cl.

Authors:  Yoshiaki Nakao; Shiro Ebata; Akira Yada; Tamejiro Hiyama; Masashi Ikawa; Sensuke Ogoshi
Journal:  J Am Chem Soc       Date:  2008-09-06       Impact factor: 15.419

2.  Palladium-catalyzed intramolecular cyanoamidation of alkynyl and alkenyl cyanoformamides.

Authors:  Yusuke Kobayashi; Haruhi Kamisaki; Reiko Yanada; Yoshiji Takemoto
Journal:  Org Lett       Date:  2006-06-22       Impact factor: 6.005

3.  Asymmetric synthesis of substituted NH-piperidines from chiral amines.

Authors:  Lekh Nath Gautam; Yijin Su; Novruz G Akhmedov; Jeffrey L Petersen; Xiaodong Shi
Journal:  Org Biomol Chem       Date:  2014-09-07       Impact factor: 3.876

4.  Catalytic C-CN bond activation.

Authors:  Yoshiaki Nakao
Journal:  Top Curr Chem       Date:  2014

5.  Enantioselective synthesis of 3,3-disubstituted oxindoles through Pd-catalyzed cyanoamidation.

Authors:  Yoshizumi Yasui; Haruhi Kamisaki; Yoshiji Takemoto
Journal:  Org Lett       Date:  2008-06-27       Impact factor: 6.005

6.  Intra- and intermolecular amidation of C-C unsaturated bonds through palladium-catalyzed reactions of carbamoyl derivatives.

Authors:  Yoshizumi Yasui; Yoshiji Takemoto
Journal:  Chem Rec       Date:  2008       Impact factor: 6.771

7.  Solvent effects and activation parameters in the competitive cleavage of C-CN and C-H bonds in 2-methyl-3-butenenitrile using [(dippe)NiH]2.

Authors:  Brett D Swartz; Nicole M Reinartz; William W Brennessel; Juventino J García; William D Jones
Journal:  J Am Chem Soc       Date:  2008-06-10       Impact factor: 15.419

8.  Synthetic studies on vincorine: access to the 3a,8a-dialkyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole skeleton.

Authors:  Yoshizumi Yasui; Tomoyo Kinugawa; Yoshiji Takemoto
Journal:  Chem Commun (Camb)       Date:  2009-06-09       Impact factor: 6.222
  8 in total
  2 in total

1.  Studies towards the total synthesis of drimentine C. Preparation of the AB and CDEF ring fragments.

Authors:  Sarah M Pound; Steven J Underwood; Christopher J Douglas
Journal:  European J Org Chem       Date:  2020-03-19

2.  Iodine-DMSO mediated conversion of N-arylcyanothioformamides to N-arylcyanoformamides and the unexpected formation of 2-cyanobenzothiazoles.

Authors:  Ziad Moussa; Zaher M A Judeh; Ahmed Alzamly; Saleh A Ahmed; Harbi Tomah Al-Masri; Bassam Al-Hindawi; Faisal Rasool; Sara Saada
Journal:  RSC Adv       Date:  2022-02-21       Impact factor: 3.361
  2 in total

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