Construction of Fused Medium-Ring Carbocycles by Catalytic Generation and Rearrangement of Oxonium Ylides

2006 ◽  
Vol 2006 (2) ◽  
pp. 323-327 ◽  
Author(s):  
J. Stephen Clark ◽  
Steven B. Walls ◽  
Claire Wilson ◽  
Stephen P. East ◽  
Martin J. Drysdale
Keyword(s):  
Oxonium Ylides ◽  
Medium Ring

Construction of Fused Medium-Ring Carbocycles by Catalytic Generation and Rearrangement of Oxonium Ylides.

ChemInform ◽  
2006 ◽  
Vol 37 (21) ◽  
Author(s):  
J. Stephen Clark ◽  
Steven B. Walls ◽  
Claire Wilson ◽  
Stephen P. East ◽  
Martin J. Drysdale
Keyword(s):  
Oxonium Ylides ◽  
Medium Ring

Diels–Alder adducts of medium-ring carbocyclic dienes prepared by rearrangement of catalytically generated cyclic oxonium ylides

2001 ◽  
Vol 57 (11) ◽  
pp. 1326-1329 ◽  
Author(s):  
Claire Wilson ◽  
J. Stephen Clark ◽  
Andrea L. Bate ◽  
Alexander J. Blake ◽  
Trevor Grinter ◽  
...  
Keyword(s):  
Diels Alder ◽  
Oxonium Ylides ◽  
Medium Ring

ChemInform Abstract: Diels-Alder Adducts of Medium-Ring Carbocyclic Dienes Prepared by Rearrangement of Catalytically Generated Cyclic Oxonium Ylides

ChemInform ◽  
2010 ◽  
Vol 33 (9) ◽  
pp. no-no
Author(s):  
Claire Wilson ◽  
J. Stephen Clark ◽  
Andrea L. Bate ◽  
Alexander J. Blake ◽  
Trevor Grinter ◽  
...  
Keyword(s):  
Diels Alder ◽  
Oxonium Ylides ◽  
Medium Ring

Medium ring ethers via [1,2]-shift of acetal-derived oxonium ylides

1998 ◽  
Vol 39 (26) ◽  
pp. 4631-4634 ◽  
Author(s):  
Richland W. Tester ◽  
F.G. West
Keyword(s):  
Oxonium Ylides ◽  
Medium Ring

ChemInform Abstract: Rapid Synthesis of Medium-Ring Fused Polycarbocyclic Systems by Rearrangement of Carbenoid-Derived Oxonium Ylides.

ChemInform ◽  
2008 ◽  
Vol 39 (9) ◽  
Author(s):  
J. Stephen Clark ◽  
Carine Guerot ◽  
Claire Wilson ◽  
Alexander J. Blake
Keyword(s):  
Rapid Synthesis ◽  
Oxonium Ylides ◽  
Medium Ring

Polycyclic oxonium ylides — Use of cyclic acetals as convenient scaffolds in the construction of fused bicyclic compounds containing a medium ring

2006 ◽  
Vol 84 (10) ◽  
pp. 1470-1486 ◽  
Author(s):  
Graham K Murphy ◽  
Fredrik P Marmsäter ◽  
F G West
Keyword(s):  
Ring Expansion ◽  
Major Product ◽  
Side Chains ◽  
Cyclic Acetals ◽  
Bicyclic Compounds ◽  
Oxonium Ylides ◽  
Sulfonium Ylide ◽  
Oxonium Ylide ◽  
Medium Ring

Cyclic mixed acetals with pendant diazoketone side chains undergo efficient rearrangement to ether-bridged cyclooctanoid and cycloheptanoid systems upon treatment with Cu(hfacac)2. Stevens [1,2]-shift of an oxonium ylide furnishes the major product, in some cases accompanied by minor amounts of a product resulting from [1,2]-shift of a sulfonium ylide. These results demonstrate that hetero-substituted carbons are suitable migrating groups for the Stevens [1,2]-shift of oxonium ylides. In cases employing a mixed thioacetal, the resulting sulfide served as a trigger for cleavage of the bridging ether through one of two complementary strategies. In the hydrazulene series, the desired bicyclo[5.3.0]heptene was accompanied by the product of novel transannular SN2′ attack on the resulting allylic ketal.Key words: [1,2]-shift, diazo, medium-sized ring, oxonium ylide, ring expansion.

ChemInform Abstract: Medium Ring Ethers via [1,2]-Shift of Acetal-Derived Oxonium Ylides.

ChemInform ◽  
2010 ◽  
Vol 29 (38) ◽  
pp. no-no
Author(s):  
R. W. TESTER ◽  
F. G. WEST
Keyword(s):  
Oxonium Ylides ◽  
Medium Ring

Rapid synthesis of medium-ring fused polycarbocyclic systems by rearrangement of carbenoid-derived oxonium ylides

2007 ◽  
pp. 4134 ◽  
Author(s):  
J. Stephen Clark ◽  
Carine Guérot ◽  
Claire Wilson ◽  
Alexander J. Blake
Keyword(s):  
Rapid Synthesis ◽  
Oxonium Ylides ◽  
Medium Ring
Sign in / Sign up

Export Citation Format

Share Document