Literature DB >> 23145913

Highly regio-, diastereo-, and enantioselective 1,6- and 1,8-additions of azlactones to di- and trienyl N-acylpyrroles.

Daisuke Uraguchi1, Ken Yoshioka, Yusuke Ueki, Takashi Ooi.   

Abstract

A vinylog of Michael addition (1,6-addition) of azlactones to δ-substituted dienyl N-acylpyrroles has been developed with virtually complete 1,6-, diastereo-, and enantioselectivities by means of chiral P-spiro triaminoiminophosphorane as a catalyst. This system has been successfully extended to an unprecedented bis-vinylog of Michael addition (1,8-addition) of azlactones to ζ-substituted trienyl N-acylpyrroles with high levels of regio- and stereocontrol.

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Year:  2012        PMID： 23145913     DOI： 10.1021/ja310209g

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  14 in total

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2.  Higher-Order Cyclopropenimine Superbases: Direct Neutral Brønsted Base Catalyzed Michael Reactions with α-Aryl Esters.

Authors:  Eric D Nacsa; Tristan H Lambert
Journal:  J Am Chem Soc       Date:  2015-08-04       Impact factor: 15.419

3.  Copper(I)-Catalyzed Asymmetric Conjugate 1,6-, 1,8-, and 1,10-Borylation.

Authors:  Chang-Yun Shi; Jungmin Eun; Timothy R Newhouse; Liang Yin
Journal:  Angew Chem Int Ed Engl       Date:  2021-03-18       Impact factor: 15.336

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5.  Preparation of macrocyclic Z-enoates and (E,Z)- or (Z,E)-dienoates through catalytic stereoselective ring-closing metathesis.

Authors:  Hanmo Zhang; Elsie C Yu; Sebastian Torker; Richard R Schrock; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2014-11-17       Impact factor: 15.419

6.  Direct Catalytic Asymmetric Doubly Vinylogous Michael Addition of α,β-Unsaturated γ-Butyrolactams to Dienones.

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Journal:  Angew Chem Int Ed Engl       Date:  2015-07-15       Impact factor: 15.336

7.  Organocatalytic synthesis of chiral tetrasubstituted allenes from racemic propargylic alcohols.

Authors:  Deyun Qian; LinLin Wu; Zhenyang Lin; Jianwei Sun
Journal:  Nat Commun       Date:  2017-09-18       Impact factor: 14.919

8.  Bifunctional iminophosphorane organocatalysts for enantioselective synthesis: application to the ketimine nitro-Mannich reaction.

Authors:  Marta G Núñez; Alistair J M Farley; Darren J Dixon
Journal:  J Am Chem Soc       Date:  2013-11-06       Impact factor: 15.419

9.  Enantioselective reductive multicomponent coupling reactions between isatins and aldehydes.

Authors:  Matthew A Horwitz; Naoya Tanaka; Takuya Yokosaka; Daisuke Uraguchi; Jeffrey S Johnson; Takashi Ooi
Journal:  Chem Sci       Date:  2015-07-30       Impact factor: 9.825

10.  Structure-Activity Relationship Studies of Cyclopropenimines as Enantioselective Brønsted Base Catalysts.

Authors:  Jeffrey S Bandar; Alexandre P Barthelme; Alon Y Mazori; Tristan H Lambert
Journal:  Chem Sci       Date:  2014-12-19       Impact factor: 9.825
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