ChemInform Abstract: Total Synthesis of (+)-Tanikolide by a Traceless Stereoinduction Method Using Rhodium(II)-Catalyzed Oxonium Ylide Formation-[2,3]-Sigmatropic Rearrangement and NHC-Catalyzed Ring-Expansion Lactonization.

ChemInform ◽  
2016 ◽  
Vol 47 (35) ◽  
Author(s):  
Hisanori Nambu ◽  
Hikari Jinnouchi ◽  
Tomoya Fujiwara ◽  
Takayuki Yakura
Keyword(s):  
Total Synthesis ◽  
Ring Expansion ◽  
Sigmatropic Rearrangement ◽  
Oxonium Ylide

Ring expansion of trans-divinyl ethylene oxide by oxonium ylide [2,3] sigmatropic rearrangement

2006 ◽  
Vol 47 (41) ◽  
pp. 7281-7283 ◽  
Author(s):  
Kevin J. Quinn ◽  
Neal A. Biddick ◽  
Brian A. DeChristopher
Keyword(s):  
Ethylene Oxide ◽  
Ring Expansion ◽  
Sigmatropic Rearrangement ◽  
Oxonium Ylide

Ring Expansion of trans-Divinyl Ethylene Oxide by Oxonium Ylide [2,3] Sigmatropic Rearrangement.

ChemInform ◽  
2007 ◽  
Vol 38 (3) ◽  
Author(s):  
Kevin J. Quinn ◽  
Neal A. Biddick ◽  
Brian A. DeChristopher
Keyword(s):  
Ethylene Oxide ◽  
Ring Expansion ◽  
Sigmatropic Rearrangement ◽  
Oxonium Ylide

Total synthesis of a protected form of sphingofungin E using the [3,3]-sigmatropic rearrangement of an allylic thiocyanate as the key reaction

2010 ◽  
Vol 345 (17) ◽  
pp. 2427-2437 ◽  
Author(s):  
Miroslava Martinková ◽  
Jozef Gonda ◽  
Jana Špaková Raschmanová ◽  
Michaela Slaninková ◽  
Juraj Kuchár
Keyword(s):  
Total Synthesis ◽  
Sigmatropic Rearrangement

scholarly journals Intermolecular 3+3 Ring Expansion of Aziridines to Dehydropiperidines through the Intermediacy of Aziridinium Ylides

2019 ◽  
Author(s):  
Jennifer Schomaker ◽  
Josephine Eshon ◽  
Kate A. Nicastri ◽  
Steven C. Schmid ◽  
William T. Raskopf ◽  
...  
Keyword(s):  
Natural Product ◽  
Functional Group ◽  
Ring Expansion ◽  
Sigmatropic Rearrangement ◽  
Reactive Intermediate ◽  
Mechanistic Studies ◽  
Reaction Conditions ◽  
Complex Molecules ◽  
Form Complex ◽  
Reaction Proceeds

Bicyclic aziridines undergo formal [3+3] ring expansion reactions when exposed to rhodium-bound vinyl carbenes to form complex dehydropiperidines in a highly stereocontrolled rearrangement. Mechanistic studies and DFT computations indicate the reaction proceeds through the formation of a vinyl aziridinium ylide; this reactive intermediate undergoes a concerted, asynchronous, pseudo-[1,4]- sigmatropic rearrangement to directly furnish the heterocyclic products with net retention at the new C-C bond. In combination with an asymmetric silver-catalyzed aziridination developed in our group, this method quickly delivers enantioenriched scaffolds with up to three contiguous stereocenters. The mild reaction conditions, functional group tolerance, and high stereochemical retention of this method are especially well-suited for appending piperidine motifs to natural product and complex molecules. Ultimately, our work establishes the value of underutilized aziridinium ylides as key intermediates in strategies to convert small, strained rings to larger N-heterocycles.

ChemInform Abstract: Stereoselective Ring Expansion of Vinyl Oxiranes: Mechanistic Insights and Natural Product Total Synthesis.

ChemInform ◽  
2010 ◽  
Vol 41 (27) ◽  
pp. no-no
Author(s):  
Matthew Brichacek ◽  
Lindsay A. Batory ◽  
Jon T. Njardarson
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Ring Expansion

Total Synthesis of Lennoxamine and Chilenine via Ring-Expansion of Iso- indoloisoquinoline to Isoindolobenz- azepine

Heterocycles ◽  
2003 ◽  
Vol 59 (2) ◽  
pp. 527 ◽  
Author(s):  
Tatsuo Nagasaka ◽  
Yuji Koseki ◽  
Shinya Katsura ◽  
Shuichi Kusano ◽  
Harumi Sakata ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Ring Expansion
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