2007
DOI: 10.1021/ol702631q
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Polyene Cyclization Promoted by the Cross-Conjugated α-Carbalkoxy Enone System. Observation on a Putative 1,5-Hydride/1,3-Alkyl Shift under Lewis Acid Catalysis

Abstract: Polyene cyclization of compounds 3 and 4 under catalysis with AlCl3 and/or SnCl4 gave rise to complex bicyclic products 8 and 9, structures of which were highly unexpected, and X-ray analyses were invoked for unambiguously structural identification. Mechanistically, a tandem sigma-bond rearrangement process, including an unusual through-space 1,5-hydride or 1,3-alkyl shift as a key operation, is proposed.

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Cited by 19 publications
(9 citation statements)
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“…The usual workup (EtOAc; brine) and purification (5–10% EtOAc in hexanes) afforded 10 (45.9 mg, 39% over two steps) as a yellow oil. Spectral data was consistent with that previously reported …”
Section: Methodssupporting
confidence: 92%
“…The usual workup (EtOAc; brine) and purification (5–10% EtOAc in hexanes) afforded 10 (45.9 mg, 39% over two steps) as a yellow oil. Spectral data was consistent with that previously reported …”
Section: Methodssupporting
confidence: 92%
“…In order to effect a polyene cyclization, Shia and co‐workers subjected diene 130 to Lewis acidic conditions at room temperature (Scheme ) 62. Instead of the expected product, the unusual bicylic structure 131 was formed as a single diastereomer in good yield.…”
Section: Ch Functionalization By Intramolecular Hydride Transfermentioning
confidence: 99%
“…As listed in Table 1, under catalysis with Lewis acid (AlCl 3 or SnCl 4 ), polyene cyclization of 115 and 116, and their corresponding regioisomers 117 and 118 gave rise to complex products in moderate to high yields, respectively [49,50]. Surprisingly, the anticipated cationic cyclization product of the individual reactions was not formed predominantly; instead, the major product was determined to possess a highly unexpected structure which was unambiguously confirmed by X-ray crystallographic analyses.…”
Section: An Unusual Through-space -Bond Tandem Rearrangementmentioning
confidence: 79%