Intramolecular [1 + 2] and [3 + 2] cycloaddition reactions of cyclopropenone ketals

Journal of the American Chemical Society

Volumn 132, Issue 25, 2010, Pages 8527-8529

  Patel, Paresma R ^a   Boger, Dale L ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; ALDEHYDES; BEARINGS (STRUCTURAL); CYCLOADDITION; KETONES; OLEFINS; TOLUENE;

CARBONYL ADDITION; CYCLOADDITION REACTION; CYCLOADDUCTS; ELECTRON DEFICIENT OLEFINS; INTRAMOLECULAR VARIANTS; REACTION CONDITIONS; SINGLE ELECTRON; STRUCTURAL FEATURE; THERMAL REACTIONS;

SUBSTRATES;

ACETAL; CYCLOPROPENONE KETAL; UNCLASSIFIED DRUG; CYCLOPROPANE DERIVATIVE; CYCLOPROPENONE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLOADDITION; X RAY ANALYSIS; CHEMISTRY; STEREOISOMERISM; TEMPERATURE;

CYCLOPROPANES; STEREOISOMERISM; TEMPERATURE;

EID: 77953895911     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja103933n     Document Type: Article

References (21)

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19. Although not the topic of this communication, the substrate preparations (see the Supporting Information) revealed the robust nature of cyclopropenone ketals and indicated that they can be carried through a range of reactions (e.g., Bu4NF, CrO3-pyr2 or TPAP, Wittig reaction, Negishi coupling) that may otherwise appear challenging.
20. The X-ray data have been deposited with the Cambridge Crystallographic Data Centre under the following accession codes: 1b, CCDC773877; 2b, CCDC775265; 3b, CCDC776316; 4b, CDCC776318; major diastereomer of 12, CDCC762696; minor diastereomer of 12, CCDC773876; 24, CCDC776317.
21. Hudlicky, T., Kutchan, T. M., and Naqvi, S. Org. React. 1985, 33, 247-335