Preorganization in Highly Enantioselective Diaza-Cope Rearrangement Reaction

2005 ◽  
Vol 127 (47) ◽  
pp. 16370-16371 ◽  
Author(s):  
Hae-Jo Kim ◽  
Hyunwoo Kim ◽  
Gamil Alhakimi ◽  
Eui June Jeong ◽  
Nirusha Thavarajah ◽  
...  
Keyword(s):  
Cope Rearrangement ◽  
Rearrangement Reaction

Stereospecific Synthesis of Alkyl-Substituted Vicinal Diamines from the Mother Diamine: Overcoming the “Intrinsic Barrier” to the Diaza-Cope Rearrangement Reaction

2009 ◽  
Vol 11 (1) ◽  
pp. 157-160 ◽  
Author(s):  
Hyunwoo Kim ◽  
Mima Staikova ◽  
Alan J. Lough ◽  
Jik Chin
Keyword(s):  
Stereospecific Synthesis ◽  
Cope Rearrangement ◽  
Rearrangement Reaction ◽  
Vicinal Diamines

ChemInform Abstract: Facile Installation of 2-Reverse Prenyl Functionality into Indoles by a Tandem N-Alkylation-Aza-Cope Rearrangement Reaction and Its Application in Synthesis.

ChemInform ◽  
2016 ◽  
Vol 47 (22) ◽  
Author(s):  
Xiaobei Chen ◽  
Huaqiang Fan ◽  
Shilei Zhang ◽  
Chenguang Yu ◽  
Wei Wang
Keyword(s):  
Cope Rearrangement ◽  
Rearrangement Reaction

A Chemoenzymatic Synthesis of the cis-Decalin Core Associated with the Novel Anti-Mitotic Agent Phomopsidin: Some Observations Concerning a High-Pressure-Promoted Diels–Alder Cycloaddition Reaction of (1S,2R)-3-Methyl-cis-1,2-dihydrocatechol and the Anionic Oxy–Cope Rearrangement of Compounds Derived from the Adduct

2004 ◽  
Vol 57 (7) ◽  
pp. 641 ◽  
Author(s):  
Martin G. Banwell ◽  
Alison J. Edwards ◽  
Malcolm D. McLeod ◽  
Scott G. Stewart
Keyword(s):  
Cycloaddition Reaction ◽  
Diels Alder ◽  
Chemoenzymatic Synthesis ◽  
Cope Rearrangement ◽  
The Novel ◽  
X Ray Diffraction ◽  
Enantiomerically Pure ◽  
X Ray ◽  
Wittig Rearrangements ◽  
Rearrangement Reaction

The enantiomerically pure and enzymatically derived cis-1,2-dihydrocatechol 2 engages in a diastereofacially selective Diels–Alder cycloaddition reaction with commercially available lactone 3 at 19 kbar to afford adduct 4, which is readily elaborated to the diene-ol 13. Treatment of this last compound with KH/18[crown]-6 resulted in successive anionic oxy-Cope and 1,2-Wittig rearrangements to afford acyloin 14 embodying the cis-decalin core associated with the natural product phomopsidin (1). Compound 16 also engages in an anionic oxy-Cope rearrangement reaction to give, depending on the molar equivalents of base used, either the cis-decalin 17 or the hexahydroindene 18. The structure of compound 18 has been established by single-crystal X-ray diffraction analysis.

Taxane Diterpene Synthesis Studies. Part 2: Towards Taxinine—Enantiospecific Construction of an AB-ring Substructure Incorporating both Quaternary Carbon Centres and Attempts to Annulate the C-ring

2004 ◽  
Vol 57 (1) ◽  
pp. 53 ◽  
Author(s):  
Martin G. Banwell ◽  
Malcolm D. McLeod ◽  
Andrew G. Riches
Keyword(s):  
Total Synthesis ◽  
Cycloaddition Reaction ◽  
Ring System ◽  
Diels Alder ◽  
Biologically Active ◽  
Allylic Oxidation ◽  
Cope Rearrangement ◽  
Rearrangement Reaction ◽  
Ab Ring ◽  
Active Natural

In connection with efforts to develop an efficient total synthesis of the biologically active natural product taxinine 1, the enzymatically-derived and monochiral cis-1,2-dihydrocatechol 7 was converted, over several steps including a Diels–Alder cycloaddition reaction, into the bicyclo[2.2.2]octan-2-one 18. Reaction of the last compound with the organocerium reagent 22 afforded the 1,5-diene 23 which engaged in an anionic oxy-Cope rearrangement reaction to give, after C-methylation of the product enolate 25, bicyclo[5.3.1]undecenone 27 embodying the AB-ring system of target 1. Two methods for allylic oxidation of such products were developed and several unsuccessful attempts to effect a cyclization reaction so as to establish the taxane C-ring are described.

Design, Development, Mechanistic Elucidation, and Rational Optimization of a Tandem Ireland Claisen/Cope Rearrangement Reaction for Rapid Access to the (Iso)Cyclocitrinol Core

2014 ◽  
Vol 136 (28) ◽  
pp. 9878-9881 ◽  
Author(s):  
Christopher W. Plummer ◽  
Carolyn S. Wei ◽  
Carrie E. Yozwiak ◽  
Arash Soheili ◽  
Sara O. Smithback ◽  
...  
Keyword(s):  
Cope Rearrangement ◽  
Design Development ◽  
Rapid Access ◽  
Rearrangement Reaction

Organic-inorganic photoelectrochemical sensor based on aza-cope rearrangement reaction for formaldehyde

2021 ◽  
Vol 330 ◽  
pp. 129342
Author(s):  
Xiaowen Feng ◽  
Quanyong Wei ◽  
Shaopeng Li ◽  
Xianzhe Wei ◽  
Xiaofeng Yang ◽  
...  
Keyword(s):  
Cope Rearrangement ◽  
Photoelectrochemical Sensor ◽  
Rearrangement Reaction

ChemInform Abstract: Diastereoselective Diaza-Cope Rearrangement Reaction.

ChemInform ◽  
2008 ◽  
Vol 39 (31) ◽  
Author(s):  
Hyunwoo Kim ◽  
Doo Seoung Choi ◽  
Cindy Pai-Hui Yen ◽  
Alan J. Lough ◽  
Choong Eui Song ◽  
...  
Keyword(s):  
Cope Rearrangement ◽  
Rearrangement Reaction

ChemInform Abstract: Design, Development, Mechanistic Elucidation, and Rational Optimization of a Tandem Ireland Claisen/Cope Rearrangement Reaction for Rapid Access to the (Iso)Cyclocitrinol Core.

ChemInform ◽  
2015 ◽  
Vol 46 (6) ◽  
pp. no-no
Author(s):  
Christopher W. Plummer ◽  
Carolyn S. Wei ◽  
Carrie E. Yozwiak ◽  
Arash Soheili ◽  
Sara O. Smithback ◽  
...  
Keyword(s):  
Cope Rearrangement ◽  
Design Development ◽  
Rapid Access ◽  
Rearrangement Reaction

scholarly journals Correction to “Design, Development, Mechanistic Elucidation, and Rational Optimization of a Tandem Ireland Claisen/Cope Rearrangement Reaction for Rapid Access to the (Iso)Cyclocitrinol Core”

2015 ◽  
Vol 137 (42) ◽  
pp. 13722-13722 ◽  
Author(s):  
Christopher W. Plummer ◽  
Carolyn S. Wei ◽  
Carrie E. Yozwiak ◽  
Arash Soheili ◽  
Sara O. Smithback ◽  
...  
Keyword(s):  
Cope Rearrangement ◽  
Design Development ◽  
Rapid Access ◽  
Rearrangement Reaction
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