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Intramolecular Conjugate Addition of α,β-Unsaturated Lactones Having an Alkanenitrile Side Chain: Stereocontrolled Construction of Carbocycles with Quaternary Carbon Atoms

Yoshimura, Fumihiko; Torizuka, Makoto; Mori, Genki et al.

Synlett, 2012, 2012(2), 251-254

Permalink : https://hdl.handle.net/2115/51017

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アクセス権
open access
URI
https://hdl.handle.net/2115/51017
タイトル
Intramolecular Conjugate Addition of α,β-Unsaturated Lactones Having an Alkanenitrile Side Chain: Stereocontrolled Construction of Carbocycles with Quaternary Carbon Atoms
著者
Yoshimura, Fumihiko ; Torizuka, Makoto ; Mori, Genki ; Tanino, Keiji
e-Rad_Researcher
70374189
著者名
Yoshimura, Fumihiko
著者名
Torizuka, Makoto
著者名
Mori, Genki
e-Rad_Researcher
40217146
著者名
Tanino, Keiji
言語
英語
キーワード
carbocycles
cyclization
Michael addition
nitriles
stereoselective synthesis
発行日
2012-01
出版者
Georg Thieme Verlag
収録物名
Synlett
巻(号)
2012(2)
ページ
251-254
抄録
An efficient method for constructing carbocycles with all-carbon quaternary stereocenters has been developed on the basis of a stereoselective cyclization reaction of α,β-unsaturated lactones having an alkanenitrile side chain. Treatment of the substrate with lithium hexamethyldisilazide (LiHMDS) in the presence of triisopropylsilyl chloride (TIPSCl) led to the generation of the corresponding α-cyano carbanion species which readily underwent an intramolecular conjugate addition reaction. It was found that the combined use of trimethylsilyl trifluoromethanesulfonate (TMSOTf) and triethylamine is also effective for the cyclization reaction without using a strong base. Interestingly, different stereochemical outcomes were observed in the two cyclization methods.
資源タイプ
学術雑誌論文
出版タイプ
Accepted Manuscript
権利情報
© 2012 Georg Thieme Verlag
PISSN
0936-5214
関連情報 (isVersionOf)
出版社版DOI
https://doi.org/10.1055/s-0031-1290074