Literature DB >> 15954764

Design, synthesis, and reactivity of 1-hydrazinodienes for use in organic synthesis.

Glenn M Sammis1, Eric M Flamme, Hao Xie, Douglas M Ho, Erik J Sorensen.   

Abstract

A new 1-hydrazinodiene (1) has been developed and utilized in Lewis acid catalyzed, intermolecular Diels-Alder reactions with various electron-deficient alkenes. The hydrazine can then be deprotected, and a molecule of methanesulfinic acid is eliminated to provide a putative diazene intermediate (4), which then spontaneously undergoes a suprafacial 1,5-sigmatropic shift to yield stereochemically complex cyclohexenes. This method has been applied to the synthesis of a constitutionally and stereochemically complex decalin derivative.

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Year:  2005        PMID： 15954764     DOI： 10.1021/ja052383c

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


  11 in total

1.  N-isopropylidene-N'-2-nitrobenzenesulfonyl hydrazine, a reagent for reduction of alcohols via the corresponding monoalkyl diazenes.

Authors:  Mohammad Movassaghi; Omar K Ahmad
Journal:  J Org Chem       Date:  2007-02-03       Impact factor: 4.354

2.  Reversal of the regiochemistry in the rhodium-catalyzed [4+3] cycloaddition between vinyldiazoacetates and dienes.

Authors:  Pablo E Guzmán; Yajing Lian; Huw M L Davies
Journal:  Angew Chem Int Ed Engl       Date:  2014-09-29       Impact factor: 15.336

3.  The catalytic asymmetric Diels-Alder reactions and post-cycloaddition reductive transpositions of 1-hydrazinodienes.

Authors:  Hao Xie; Glenn M Sammis; Eric M Flamme; Christina M Kraml; Erik J Sorensen
Journal:  Chemistry       Date:  2011-09-05       Impact factor: 5.236

4.  Asymmetric Traceless Petasis Borono-Mannich Reactions of Enals: Reductive Transposition of Allylic Diazenes.

Authors:  Yao Jiang; Regan J Thomson; Scott E Schaus
Journal:  Angew Chem Int Ed Engl       Date:  2017-12-04       Impact factor: 15.336

5.  Acyclic 1,4-stereocontrol via reductive 1,3-transpositions.

Authors:  Wei Qi; Matthias C McIntosh
Journal:  Org Lett       Date:  2007-12-20       Impact factor: 6.005

6.  Preparation of n-Isopropylidene-n'-2-Nitrobenzenesulfonyl Hydrazine (IPNBSH) and Its Use in Palladium-catalyzed Synthesis of Monoalkyl Diazenes. Synthesis of 9-Allylanthracene.

Authors:  Jens Willwacher; Omar K Ahmad; Mohammad Movassaghi; Juliane Keilitz; Mark Lautens
Journal:  Organic Synth       Date:  2011-12-02

7.  Diels-Alder exo selectivity in terminal-substituted dienes and dienophiles: experimental discoveries and computational explanations.

Authors:  Yu-hong Lam; Paul Ha-Yeon Cheong; José M Blasco Mata; Steven J Stanway; Véronique Gouverneur; K N Houk
Journal:  J Am Chem Soc       Date:  2009-02-11       Impact factor: 15.419

8.  Permuting Diels-Alder and Robinson Annulation Stereopatterns.

Authors:  Feng Peng; Mingji Dai; Angie R Angeles; Samuel J Danishefsky
Journal:  Chem Sci       Date:  2012-08-01       Impact factor: 9.825

9.  Unconventional exo selectivity in thermal normal-electron-demand Diels-Alder reactions.

Authors:  Guo-Ming Ho; Ci-Jhang Huang; Elise Yu-Tzu Li; Sheng-Kai Hsu; Ti Wu; Medel Manuel L Zulueta; Kevin Binchia Wu; Shang-Cheng Hung
Journal:  Sci Rep       Date:  2016-10-12       Impact factor: 4.379

Review 10.  Chiral Diol-Based Organocatalysts in Enantioselective Reactions.

Authors:  Truong N Nguyen; Po-An Chen; Krit Setthakarn; Jeremy A May
Journal:  Molecules       Date:  2018-09-11       Impact factor: 4.411
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