Literature DB >> 23565328

Catalytic Asymmetric Synthesis of Highly Substituted Pyrrolizidines.

Andrew D Lim1, Julian A Codelli, Sarah E Reisman.   

Abstract

A catalytic asymmetric double (1,3)-dipolar cycloaddition reaction has been developed. Using a chiral silver catalyst, enantioenriched pyrrolizidines can be prepared in one flask from inexpensive, commercially available starting materials. The pyrrolizidine products contain a variety of substitution patterns and as many as six stereogenic centers.

Entities:  

Year:  2012        PMID： 23565328      PMCID： PMC3614418          DOI： 10.1039/C2SC21617E

Source DB:  PubMed          Journal:  Chem Sci        ISSN： 2041-6520            Impact factor:   9.825


  23 in total

1.  N-(2-pyridylmethyl)imines as azomethine precursors in catalytic asymmetric [3 + 2] cycloadditions.

Authors:  Silvia Padilla; Rubén Tejero; Javier Adrio; Juan C Carretero
Journal:  Org Lett       Date:  2010-11-15       Impact factor: 6.005

2.  Identification of SK-951, a novel benzofuran derivative, as an agonist to 5-HT4 receptors.

Authors:  M Takeda; K Tsukamoto; Y Mizutani; T Suzuki; K Taniyama
Journal:  Jpn J Pharmacol       Date:  1999-02

3.  Construction of enantiopure pyrrolidine ring system via asymmetric [3+2]-cycloaddition of azomethine ylides.

Authors:  Ganesh Pandey; Prabal Banerjee; Smita R Gadre
Journal:  Chem Rev       Date:  2006-11       Impact factor: 60.622

4.  Cu(I)-catalyzed highly exo-selective and enantioselective [3 + 2] cycloaddition of azomethine ylides with acrylates.

Authors:  Wenzhong Gao; Xumu Zhang; Malati Raghunath
Journal:  Org Lett       Date:  2005-09-15       Impact factor: 6.005

5.  Enantioselective total synthesis of (-)-acetylaranotin, a dihydrooxepine epidithiodiketopiperazine.

Authors:  Julian A Codelli; Angela L A Puchlopek; Sarah E Reisman
Journal:  J Am Chem Soc       Date:  2011-10-28       Impact factor: 15.419

6.  Chiral silver amide catalyst for the [3+2] cycloaddition of α-amino esters to olefins.

Authors:  Yasuhiro Yamashita; Takaki Imaizumi; Shū Kobayashi
Journal:  Angew Chem Int Ed Engl       Date:  2011-04-06       Impact factor: 15.336

7.  Alkaloids from bufonid toads (Melanophryniscus): decahydroquinolines, pumiliotoxins and homopumiliotoxins, indolizidines, pyrrolizidines, and quinolizidines.

Authors:  H M Garraffo; T F Spande; J W Daly; A Baldessari; E G Gros
Journal:  J Nat Prod       Date:  1993-03       Impact factor: 4.050

8.  Catalytic asymmetric [3+2] cycloaddition of azomethine ylides. Development of a versatile stepwise, three-component reaction for diversity-oriented synthesis.

Authors:  Chuo Chen; Xiaodong Li; Stuart L Schreiber
Journal:  J Am Chem Soc       Date:  2003-08-27       Impact factor: 15.419

9.  Fused bicyclic pyrrolizinones as new scaffolds for human NK1 antagonists.

Authors:  Gregori J Morriello; Robert J Devita; Sander G Mills; Jonathan R Young; Peter Lin; George Doss; Gary G Chicchi; Julie Demartino; Marc M Kurtz; Kwei-Lan C Tsao; Emma Carlson; Karen Townson; Alan Wheeldon; Susan Boyce; Neil Collinson; Nadia Rupniak; Stephen Moore
Journal:  Bioorg Med Chem       Date:  2007-12-05       Impact factor: 3.641

10.  Stereocontrolled cyclic nitrone cycloaddition strategy for the synthesis of pyrrolizidine and indolizidine alkaloids.

Authors:  Alberto Brandi; Francesca Cardona; Stefano Cicchi; Franca M Cordero; Andrea Goti
Journal:  Chemistry       Date:  2009-08-10       Impact factor: 5.236
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  2 in total

1.  Enantioselective Synthesis of (-)-Acetylapoaranotin.

Authors:  Haoxuan Wang; Clinton J Regan; Julian A Codelli; Paola Romanato; Angela L A Puchlopek-Dermenci; Sarah E Reisman
Journal:  Org Lett       Date:  2017-03-28       Impact factor: 6.005

2.  Catalytic enantioselective 1,3-dipolar cycloadditions of azomethine ylides for biology-oriented synthesis.

Authors:  Rishikesh Narayan; Marco Potowski; Zhi-Jun Jia; Andrey P Antonchick; Herbert Waldmann
Journal:  Acc Chem Res       Date:  2014-03-22       Impact factor: 22.384
  2 in total

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