Facile construction of novel polycyclic ring systems using a metallocarbenoid-induced cyclization of acetylenic diazo carbonyl compounds

Organic Letters

Volumn 2, Issue 14, 2000, Pages 2093-2095

  Padwa, Albert ^a   Straub, Christopher S ^a  

^a EMORY UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000848767     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006004q     Document Type: Article

References (29)

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23. All new compounds in this study were fully characterized (IR, NMR, elemental analysis, and/or HRMS). A combination of DQF-COSY, HMBC, and HMQC NMR experiments were used to assign the stereochemistry of the rearranged IMDAF products.
24. An alternate possibility to rationalize the formation of 21 would involve proton loss from the α-position of 25a followed by a rapid 1,5-sigmatropic hydrogen shift of the resulting cyclohexadienol to give enol 26a.
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28. Diazo β-alkoxy esters such as 16 or 17 require the presence of a trimethylsilyl group on the alkyne carbon for efficient cyclization to occur. In contrast, diazo β-amido esters such as 31 undergo efficient reorganization to 2-amino substituted furans using simple terminal alkynes.
29. By carrying out the thermolysis of 31 at 80°C, it was possible to isolate the expected o-cyclopentenyl phenoxy substituted furan in 94% yield. Further heating of this furan at 145°C afforded 32 in 45% isolated yield.