Literature DB >> 23320852

Synthesis of isoquinuclidines from highly substituted dihydropyridines via the Diels-Alder reaction.

Rhia M Martin1, Robert G Bergman, Jonathan A Ellman.   

Abstract

A stereo- and regioselective Diels-Alder reaction for the synthesis of highly substituted isoquinuclidines from dihydropyridines and electron-deficient alkenes has been developed. While reactions with activated dienophiles proceed readily under thermal conditions, the use of Lewis acid additives is necessary to facilitate cycloadditions for less reactive alkenes. This procedure affords the target compounds in high yields and diastereoselectivities.

Entities:  

Mesh：

Substances：

Year:  2013        PMID： 23320852      PMCID： PMC3570756          DOI： 10.1021/ol303040r

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  35 in total

1.  Synthetic strategy toward skeletal diversity via solid-supported, otherwise unstable reactive intermediates.

Authors:  Steven J Taylor; Alexander M Taylor; Stuart L Schreiber
Journal:  Angew Chem Int Ed Engl       Date:  2004-03-19       Impact factor: 15.336

2.  A novel chiral oxazolidine organocatalyst for the synthesis of an oseltamivir intermediate using a highly enantioselective Diels-Alder reaction of 1,2-dihydropyridine.

Authors:  Hiroto Nakano; Kenichi Osone; Mitsuhiro Takeshita; Eunsang Kwon; Chigusa Seki; Haruo Matsuyama; Nobuhiro Takano; Yoshihito Kohari
Journal:  Chem Commun (Camb)       Date:  2010-05-26       Impact factor: 6.222

3.  Oxidative coupling of aromatic substrates with alkynes and alkenes under rhodium catalysis.

Authors:  Tetsuya Satoh; Masahiro Miura
Journal:  Chemistry       Date:  2010-10-04       Impact factor: 5.236

Review 4.  Towards mild metal-catalyzed C-H bond activation.

Authors:  Joanna Wencel-Delord; Thomas Dröge; Fan Liu; Frank Glorius
Journal:  Chem Soc Rev       Date:  2011-06-10       Impact factor: 54.564

5.  [4 + 2] Cyclocondensation reactions of tungsten-dihydropyridine complexes and the generation of tri- and tetrasubstituted piperidines.

Authors:  Daniel P Harrison; Diana A Iovan; William H Myers; Michal Sabat; Sisi Wang; Victor E Zottig; W Dean Harman
Journal:  J Am Chem Soc       Date:  2011-10-26       Impact factor: 15.419

6.  Stereoselective synthesis of 2,3,6-trisubstituted tetrahydropyridines via Tf(2)O-mediated Grob fragmentation: access to indolizidines (-)-209I and (-)-223J.

Authors:  Gérald Lemonnier; André B Charette
Journal:  J Org Chem       Date:  2010-11-05       Impact factor: 4.354

7.  Total synthesis of (+)-lepadin B: stereoselective synthesis of nonracemic polysubstituted hydroquinolines using an RC-ROM process.

Authors:  Guillaume Barbe; André B Charette
Journal:  J Am Chem Soc       Date:  2008-09-27       Impact factor: 15.419

8.  A convenient domino access to substituted alkyl 1,2-dihydropyridine-3-carboxylates from propargyl enol ethers and primary amines.

Authors:  David Tejedor; Gabriela Méndez-Abt; Fernando García-Tellado
Journal:  Chemistry       Date:  2010-01-11       Impact factor: 5.236

9.  Cross-dehydrogenative coupling (CDC): exploring C-C bond formations beyond functional group transformations.

Authors:  Chao-Jun Li
Journal:  Acc Chem Res       Date:  2009-02-17       Impact factor: 22.384

10.  Silver ion-induced Grob fragmentation of gamma-amino iodides: highly stereoselective synthesis of polysubstituted piperidines.

Authors:  Guillaume Barbe; Miguel St-Onge; André B Charette
Journal:  Org Lett       Date:  2008-12-04       Impact factor: 6.005
View more
  6 in total

1.  Rh(I)-Catalyzed Cycloisomerization of 1,6-Enynes.

Authors:  Yuji Matsushima; Eric M Phillips; Robert G Bergman; Jonathan A Ellman
Journal:  Synlett       Date:  2015-02-27       Impact factor: 2.454

Review 2.  Rhodium-Catalyzed C-H Alkenylation/Electrocyclization Cascade Provides Dihydropyridines That Serve as Versatile Intermediates to Diverse Nitrogen Heterocycles.

Authors:  Sun Dongbang; Danielle N Confair; Jonathan A Ellman
Journal:  Acc Chem Res       Date:  2021-03-19       Impact factor: 22.384

3.  Stereoselective synthesis of isoquinuclidines through an aza-[4 + 2] cycloaddition of chiral cyclic 2-amidodienes.

Authors:  Li-Chao Fang; Richard P Hsung
Journal:  Org Lett       Date:  2014-03-12       Impact factor: 6.005

Review 4.  Preparative Synthesis of Highly Substituted Tetrahydropyridines via a Rh(I)-Catalyzed C-H Functionalization Sequence.

Authors:  Tehetena Mesganaw; Jonathan A Ellman
Journal:  Org Process Res Dev       Date:  2014-08-29       Impact factor: 3.317

Review 5.  Convergent Synthesis of Diverse Tetrahydropyridines via Rh(I)-Catalyzed C-H Functionalization Sequences.

Authors:  Tehetena Mesganaw; Jonathan A Ellman
Journal:  Org Process Res Dev       Date:  2014-08-29       Impact factor: 3.317

6.  A General Iridium-Catalyzed Reductive Dienamine Synthesis Allows a Five-Step Synthesis of Catharanthine via the Elusive Dehydrosecodine.

Authors:  Pablo Gabriel; Yaseen A Almehmadi; Zeng Rong Wong; Darren J Dixon
Journal:  J Am Chem Soc       Date:  2021-07-13       Impact factor: 15.419
  6 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.