Design of an Organocatalytic Asymmetric (4+3) Cycloaddition of2-Indolylalcohols with Dienolsilanes

Ouyang, Jie; Maji, Rajat; Leutzsch, Markus et al.

Journal of the American Chemical Society, 2022, 144(19), 8460-8466

Permalink : https://hdl.handle.net/2115/86369

このアイテムのアクセス数:484件（2026-01-14 07:22 集計）

ファイル	フォーマット	サイズ	閲覧回数	説明
https://doi.org/10.1021/jacs.2c02216

アクセス権	metadata only access
URI	https://hdl.handle.net/2115/86369
タイトル	Design of an Organocatalytic Asymmetric (4+3) Cycloaddition of2-Indolylalcohols with Dienolsilanes
著者	Ouyang, Jie ; Maji, Rajat ; Leutzsch, Markus ; Mitschke, Benjamin ; List, Benjamin
著者名 Ouyang, Jie
著者名 Maji, Rajat
著者名 Leutzsch, Markus
著者名 Mitschke, Benjamin
e-Rad_Researcher 80899253 著者名 List, Benjamin
言語	英語
キーワード	Addition reactions
	Alcohols
	Catalysts
	Cyclization
	Stereoselectivity
発行日	2022-05-06
出版者	American Chemical Society
収録物名	Journal of the American Chemical Society
巻(号)	144(19)
ページ	8460-8466
抄録	Here we present the design of a highly enantioselective, catalytic (4 + 3) cycloaddition ofgem-dialkyl 2-indolylalcohols and dienolsilanes, enabled by strong and confined IDPi Lewis acids. The method furnishes novel bicyclo[3.2.2]cyclohepta-[b]indoles with up to three stereogenic centers, one of which is quaternary. A broad substrate scope is accompanied by versatiledownstream chemical modifications. Density functional theory-supported mechanistic studies shed light on the importance of the insitu generated silylium species in an overall concerted yet asynchronous cycloaddition.
資源タイプ	学術雑誌論文
出版タイプ	Version of Record
PISSN	0002-7863
関連情報 (isIdenticalTo)	出版社版DOI https://doi.org/10.1021/jacs.2c02216