Enantioselective Construction of a 2,8-Dioxabicyclo[3.2.1]octane Ring System via [2,3]-Sigmatropic Rearrangement of Oxonium Ylide Using Chiral Dirhodium(II) Carboxylates

2009 ◽  
Vol 38 (5) ◽  
pp. 488-489 ◽  
Author(s):  
Naoyuki Shimada ◽  
Seiichi Nakamura ◽  
Masahiro Anada ◽  
Motoo Shiro ◽  
Shunichi Hashimoto
Keyword(s):  
Ring System ◽  
Sigmatropic Rearrangement ◽  
Oxonium Ylide

Regiospecific preparation of 10-allyl-1-ketoquinolizidine and an unexpected disproportionation during its Wolff–Kischner reduction

1979 ◽  
Vol 57 (16) ◽  
pp. 2114-2117 ◽  
Author(s):  
John M. McIntosh
Keyword(s):  
Ring System ◽  
Sigmatropic Rearrangement ◽  
High Yield ◽  
Reaction Conditions ◽  
Fused Ring ◽  
Fused Ring System

Regiospecific formation of 10-allyl-1-ketoquinolizidine (7) is achieved in high yield by a [2.3] sigmatropic rearrangement of N-allyl-1-ketoquinolizidinium bromide (6). Wolff–Kischner reduction of 7 affords 10-allylquinolizidine (8) contaminated by the 10-propyl and 10-ethynyl analogs in amounts which depend on the reaction conditions. The carbon-13 spectrum of 8 indicates a trans-fused ring system with an axial substituent at C-10.

Stereoselective Construction of an Unprecedented 7−8 Fused Ring System in Micrandilactone A by [3,3]-Sigmatropic Rearrangement

2008 ◽  
Vol 10 (4) ◽  
pp. 665-668 ◽  
Author(s):  
Yan-Dong Zhang ◽  
Wei-Wu Ren ◽  
Yu Lan ◽  
Qing Xiao ◽  
Kai Wang ◽  
...  
Keyword(s):  
Ring System ◽  
Sigmatropic Rearrangement ◽  
Fused Ring ◽  
Fused Ring System

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

scholarly journals Intramolecular Oxonium Ylide Formation–[2,3] Sigmatropic Rearrangement of Diazocarbonyl-Substituted Cyclic Unsaturated Acetals: A Formal Synthesis of Hyperolactone C

2014 ◽  
Vol 79 (20) ◽  
pp. 9728-9734 ◽  
Author(s):  
David M. Hodgson ◽  
Stanislav Man ◽  
Kimberley J. Powell ◽  
Ziga Perko ◽  
Minxiang Zeng ◽  
...  
Keyword(s):  
Sigmatropic Rearrangement ◽  
Formal Synthesis ◽  
Oxonium Ylide
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