Literature DB >> 27564224

Palladium-Catalyzed Enantioselective Heteroannulation of 1,3-Dienes by Functionally Substituted Aryl Iodides.

Shu-Sen Chen1, Jing Meng1, Yu-Hui Li1, Zhi-Yong Han1.   

Abstract

The first enantioselective heteroannulation of 1,3-dienes by 2-iodoanilines and 2-iodobenzylic alcohols is described. The application of a BINOL-derived phosphoramidite ligand bearing electron-withdrawing substituents is the key to obtaining high enantioselectivity. This protocol provides an efficient way to access optically active chiral indolines and isochromans from readily available starting materials.

Entities:  

Year:  2016        PMID： 27564224     DOI： 10.1021/acs.joc.6b01611

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  7 in total

1.  Photoinduced Palladium-Catalyzed Carbofunctionalization of Conjugated Dienes Proceeding via Radical-Polar Crossover Scenario: 1,2-Aminoalkylation and Beyond.

Authors:  Kelvin Pak Shing Cheung; Daria Kurandina; Tetsuji Yata; Vladimir Gevorgyan
Journal:  J Am Chem Soc       Date:  2020-05-19       Impact factor: 15.419

2.  Mapping Ambiphile Reactivity Trends in the Anti-(Hetero)annulation of Non-Conjugated Alkenes via PdII /PdIV Catalysis.

Authors:  Hui-Qi Ni; Phillippa Cooper; Shouliang Yang; Fen Wang; Neal Sach; Pranali G Bedekar; Joyann S Donaldson; Michelle Tran-Dubé; Indrawan J McAlpine; Keary M Engle
Journal:  Angew Chem Int Ed Engl       Date:  2022-02-02       Impact factor: 15.336

3.  Highly regioselective and diastereodivergent aminomethylative annulation of dienyl alcohols enabled by a hydrogen-bonding assisting effect.

Authors:  Yao Huang; Suchen Zou; Bangkui Yu; Xuyang Yan; Song Liu; Hanmin Huang
Journal:  Chem Sci       Date:  2022-02-02       Impact factor: 9.825

4.  Pd-Catalyzed Heteroannulation Using N-Arylureas as a Sterically Undemanding Ligand Platform.

Authors:  Jakub Vaith; Dasha Rodina; Gregory C Spaulding; Shauna M Paradine
Journal:  J Am Chem Soc       Date:  2022-04-05       Impact factor: 16.383

5.  Convergent Synthesis of Dihydrobenzofurans via Urea Ligand-Enabled Heteroannulation of 2-Bromophenols with 1,3-Dienes.

Authors:  Kaitlyn E Houghtling; Amanda M Canfield; Shauna M Paradine
Journal:  Org Lett       Date:  2022-07-29       Impact factor: 6.072

6.  Construction of azaheterocycles via Pd-catalyzed migratory cycloannulation reaction of unactivated alkenes.

Authors:  Jin-Ping Wang; Shuo Song; Yichen Wu; Peng Wang
Journal:  Nat Commun       Date:  2022-08-27       Impact factor: 17.694

7.  Recent advances in palladium-catalyzed (hetero)annulation of C[double bond, length as m-dash]C bonds with ambiphilic organo(pseudo)halides.

Authors:  Hui-Qi Ni; Phillippa Cooper; Keary M Engle
Journal:  Chem Commun (Camb)       Date:  2021-08-03       Impact factor: 6.065
  7 in total

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