- Abstract:
-
Rh(II)-catalyzed oxonium ylide formation-[2,3] sigmatropic rearrangement of α-diazo-β-ketoesters possessing γ-cyclic unsaturated acetal substitution, followed by acid-catalyzed elimination-lactonization, provides a concise approach to 1,7-dioxaspiro[4.4]non-2-ene-4,6-diones. The process creates adjacent quaternary stereocenters with full control of the relative stereochemistry. An unsymmetrical monomethylated cyclic unsaturated acetal leads to hyperolactone C, where ylide formation-rearrangem...
Expand abstract - Publication status:
- Published
- Publisher copy:
- 10.1021/jo501893r
-
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- Publisher:
- American Chemical Society
- Journal:
- The Journal of organic chemistry
- Volume:
- 79
- Issue:
- 20
- Pages:
- 9728-9734
- Publication date:
- 2014-10-05
- DOI:
- EISSN:
-
1520-6904
- ISSN:
-
0022-3263
- URN:
-
uuid:df2e4027-ee49-4001-b390-5656d0bde933
- Source identifiers:
-
486001
- Local pid:
- pubs:486001
- Language:
- English
- Copyright date:
- 2014
Journal article
Intramolecular oxonium ylide formation-[2,3] sigmatropic rearrangement of diazocarbonyl-substituted cyclic unsaturated acetals: a formal synthesis of hyperolactone C.
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