Unusual Transposition of Allenic Framework in Intramolecular Cyclization of Acetal-Tethered (Allenylmethyl)silanes

Unusual Transposition of Allenic Framework in Intramolecular Cyclization of Acetal-Tethered (Allenylmethyl)silanes

Treatment of acetal-tethered (allenylmethyl)silanes, which were obtained from the corresponding 3-bromo-5-silyl-1,3-pentadienes by a Pd-catalyzed reaction with an acetal-tethered malonate, with TiCl4 gave not only vinylcyclohexene derivatives via a standard SE2′ pathway but also unusual allenylcyclo...

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Veröffentlicht in:Organic letters 2009-09, Vol.11 (18), p.4240-4243
Hauptverfasser: Ogasawara, Masamichi, Okada, Atsushi, Murakami, Hidetoshi, Watanabe, Susumu, Ge, Yonghui, Takahashi, Tamotsu
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container_end_page 4243
container_issue 18
container_start_page 4240
container_title Organic letters
container_volume 11
creator Ogasawara, Masamichi
Okada, Atsushi
Murakami, Hidetoshi
Watanabe, Susumu
Ge, Yonghui
Takahashi, Tamotsu
description Treatment of acetal-tethered (allenylmethyl)silanes, which were obtained from the corresponding 3-bromo-5-silyl-1,3-pentadienes by a Pd-catalyzed reaction with an acetal-tethered malonate, with TiCl4 gave not only vinylcyclohexene derivatives via a standard SE2′ pathway but also unusual allenylcyclopentane species via cyclization at the δ-position. Deuterium-labeling experiments revealed participation of a 1,2-hydride shift in a carbocation intermediate for the formation of the latter products.
doi_str_mv 10.1021/ol901780d
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title Unusual Transposition of Allenic Framework in Intramolecular Cyclization of Acetal-Tethered (Allenylmethyl)silanes
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