Literature DB >> 21612235

Oppolzer-type intramolecular Diels-Alder cycloadditions via isomerizations of allenamides.

John B Feltenberger1, Richard P Hsung.   

Abstract

A new approach to Oppolzer's intramolecular Diels-Alder cycloaddition (IMDA) through γ-isomerization of readily available N-tethered allenamides is described. These IMDA reactions are carried out in tandem with the allenamide isomerization or 1,3-H shift, leading to complex nitrogen heterocycles in a highly stereoselective manner.
© 2011 American Chemical Society

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Year:  2011        PMID： 21612235      PMCID： PMC3112474          DOI： 10.1021/ol2010227

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


  33 in total

1.  The total synthesis of (+/-)-pumiliotoxin-C.

Authors:  W Oppolzer; W Fröstl
Journal:  Helv Chim Acta       Date:  1975-03-12       Impact factor: 2.164

2.  Oxidation of alpha-alkoxy allenes into alpha'-alkoxy enones.

Authors:  Pierre Cordier; Corinne Aubert; Max Malacria; Vincent Gandon; Emmanuel Lacôte
Journal:  Chemistry       Date:  2010-09-03       Impact factor: 5.236

3.  Stereoselective 6π-electron electrocyclic ring closures of 2-halo-amidotrienes via a remote 1,6-asymmetric induction.

Authors:  Ryuji Hayashi; Mary C Walton; Richard P Hsung; John H Schwab; Xueliang Yu
Journal:  Org Lett       Date:  2010-11-19       Impact factor: 6.005

4.  Enamide-olefin ring-closing metathesis.

Authors:  S S Kinderman; J H van Maarseveen; H E Schoemaker; H Hiemstra; F P Rutjes
Journal:  Org Lett       Date:  2001-06-28       Impact factor: 6.005

5.  Tunable Pd-catalyzed cyclization of indole-2-carboxylic acid allenamides: carboamination vs microwave-assisted hydroamination.

Authors:  Egle M Beccalli; Alice Bernasconi; Elena Borsini; Gianluigi Broggini; Micol Rigamonti; Gaetano Zecchi
Journal:  J Org Chem       Date:  2010-10-15       Impact factor: 4.354

6.  Tandem reaction of propargylic alcohol, sulfonamide, and N-iodosuccinimide: synthesis of N-(2-iodoinden-1-yl)arenesulfonamide.

Authors:  Yuanxun Zhu; Guangwei Yin; Deng Hong; Ping Lu; Yanguang Wang
Journal:  Org Lett       Date:  2011-01-26       Impact factor: 6.005

7.  An efficient approach to Aspidosperma alkaloids via [4 + 2] cycloadditions of aminosiloxydienes: stereocontrolled total synthesis of (+/-)-tabersonine. Gram-scale catalytic asymmetric syntheses of (+)-tabersonine and (+)-16-methoxytabersonine. Asymmetric syntheses of (+)-aspidospermidine and (-)-quebrachamine.

Authors:  Sergey A Kozmin; Tetsuo Iwama; Yong Huang; Viresh H Rawal
Journal:  J Am Chem Soc       Date:  2002-05-01       Impact factor: 15.419

8.  Enamide-benzyne-[2 + 2] cycloaddition: stereoselective tandem [2 + 2]-pericyclic ring-opening-intramolecular N-tethered [4 + 2] cycloadditions.

Authors:  John B Feltenberger; Ryuji Hayashi; Yu Tang; Eric S C Babiash; Richard P Hsung
Journal:  Org Lett       Date:  2009-08-20       Impact factor: 6.005

9.  A general synthetic entry to the pentacyclic strychnos alkaloid family, using a [4 + 2]-cycloaddition/rearrangement cascade sequence.

Authors:  Jutatip Boonsombat; Hongjun Zhang; Majid J Chughtai; John Hartung; Albert Padwa
Journal:  J Org Chem       Date:  2008-04-01       Impact factor: 4.354

10.  Epimeric cis-decahydroquinoline-5-carboxylic acids: effects on gamma-aminobutyric acid uptake and receptor binding in vitro.

Authors:  D T Witiak; K Tomita; R J Patch; S J Enna
Journal:  J Med Chem       Date:  1981-07       Impact factor: 7.446
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  5 in total

1.  A highly stereoselective Diels-Alder cycloaddition of enones with chiral cyclic 2-amidodienes derived from allenamides.

Authors:  Li-Chao Fang; Richard P Hsung; Zhi-Xiong Ma; William R Presser
Journal:  Org Lett       Date:  2013-09-03       Impact factor: 6.005

2.  Facile Synthesis of 3-Amido-Dienynes via a Tandem α-Propargylation-Isomerization of Chiral Allenamides and their Applications in Diels-Alder Cycloadditions.

Authors:  Zhi-Xiong Ma; Li-Chao Fang; Richard P Hsung
Journal:  Synlett       Date:  2017-09-01       Impact factor: 2.454

Review 3.  Allenamides: a powerful and versatile building block in organic synthesis.

Authors:  Ting Lu; Zhenjie Lu; Zhi-Xiong Ma; Yu Zhang; Richard P Hsung
Journal:  Chem Rev       Date:  2013-04-04       Impact factor: 60.622

4.  Total syntheses of chelidonine and norchelidonine via an enamide-benzyne-[2 + 2] cycloaddition cascade.

Authors:  Zhi-Xiong Ma; John B Feltenberger; Richard P Hsung
Journal:  Org Lett       Date:  2012-05-10       Impact factor: 6.005

Review 5.  Recent progress in transition-metal-free functionalization of allenamides.

Authors:  Xiaoxiao Li; Yongchun Liu; Na Ding; Xiaoju Tan; Zhigang Zhao
Journal:  RSC Adv       Date:  2020-10-06       Impact factor: 3.361
  5 in total

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