Force-Transformed Free-Energy Surfaces and Trajectory-Shooting Simulations Reveal the Mechano-Stereochemistry of Cyclopropane Ring-Opening Reactions

2011 ◽  
Vol 123 (31) ◽  
pp. 7243-7246 ◽  
Author(s):  
Przemyslaw Dopieralski ◽  
Jordi Ribas-Arino ◽  
Dominik Marx
Keyword(s):  
Free Energy ◽  
Ring Opening ◽  
Cyclopropane Ring ◽  
Ring Opening Reactions ◽  
Energy Surfaces

scholarly journals Stereoselective Cyclopropane Ring Opening Reactions of Nortricyclene Hydrocarbons in Formic Acid. I. Reactions of Nortricyclene, Norbornene and Tricyclene.

1973 ◽  
Vol 27 ◽  
pp. 374-376 ◽  
Author(s):  
Jaakko Paasivirta ◽  
Cecilia Kierkegaard ◽  
Jan Pappas ◽  
Steen Skaarup ◽  
Riitta Aaltonen ◽  
...  
Keyword(s):  
Formic Acid ◽  
Ring Opening ◽  
Cyclopropane Ring ◽  
Ring Opening Reactions

scholarly journals Investigations of Ring-Opening Reactions of Cyclopropanated Carbohydrates: Towards the Synthesis of the Natural Product (--)-TAN-2483B

2021 ◽  
Author(s):  
◽  
Russell James Hewitt
Keyword(s):  
Natural Product ◽  
Ring Opening ◽  
Cyclopropane Ring ◽  
Ring Expansion ◽  
Ring Opening Reactions ◽  
The Subject ◽  
The Many

<p>Cyclopropanes and carbohydrates are materials of great interest to chemists. Ring opening reactions of cyclopropanated carbohydrates have excellent potential for synthesis, due to the many diverse structures that may be obtained. The work described in this thesis explores the scope of such ring opening reactions, and extends to the synthesis and reactions of several novel cyclopropanated carbohydrates, in which synthesis of a natural product was also investigated. Several bicyclic gem-dihalocyclopropanes, including 97, were synthesised. Base-mediated cyclopropane ring opening of 97 in the presence of nucleophiles afforded a series of 2-C-branched glycosides 389 and 390 (Chapter 2), whereas silver-promoted ring expansion provided access to seven-membered rings (255 and 256) (Chapter 3). Studies on the mechanisms of the ring opening processes were also carried out. Ring-opening reactions of carbohydrate-derived gem-dihalocyclopropanes were also applied to the exploration of possible routes to the natural product (--)-TAN-2483B (154). Attempts to convert d-galactose and d-xylose into the dihydropyran 193 are the subject of Chapter 4, while the transformation of d-mannose into 193 and subsequent efforts to prepare the natural product 154 are discussed in Chapter 5.</p>

scholarly journals Investigations of Ring-Opening Reactions of Cyclopropanated Carbohydrates: Towards the Synthesis of the Natural Product (--)-TAN-2483B

2021 ◽  
Author(s):  
◽  
Russell James Hewitt
Keyword(s):  
Natural Product ◽  
Ring Opening ◽  
Cyclopropane Ring ◽  
Ring Expansion ◽  
Ring Opening Reactions ◽  
The Subject ◽  
The Many

<p>Cyclopropanes and carbohydrates are materials of great interest to chemists. Ring opening reactions of cyclopropanated carbohydrates have excellent potential for synthesis, due to the many diverse structures that may be obtained. The work described in this thesis explores the scope of such ring opening reactions, and extends to the synthesis and reactions of several novel cyclopropanated carbohydrates, in which synthesis of a natural product was also investigated. Several bicyclic gem-dihalocyclopropanes, including 97, were synthesised. Base-mediated cyclopropane ring opening of 97 in the presence of nucleophiles afforded a series of 2-C-branched glycosides 389 and 390 (Chapter 2), whereas silver-promoted ring expansion provided access to seven-membered rings (255 and 256) (Chapter 3). Studies on the mechanisms of the ring opening processes were also carried out. Ring-opening reactions of carbohydrate-derived gem-dihalocyclopropanes were also applied to the exploration of possible routes to the natural product (--)-TAN-2483B (154). Attempts to convert d-galactose and d-xylose into the dihydropyran 193 are the subject of Chapter 4, while the transformation of d-mannose into 193 and subsequent efforts to prepare the natural product 154 are discussed in Chapter 5.</p>

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