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


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Title:	Design of an Organocatalytic Asymmetric (4+3) Cycloaddition of2-Indolylalcohols with Dienolsilanes
Authors:	Ouyang, Jie Browse this author
	Maji, Rajat Browse this author
	Leutzsch, Markus Browse this author
	Mitschke, Benjamin Browse this author
	List, Benjamin Browse this author →KAKEN DB
Keywords:	Addition reactions
	Alcohols
	Catalysts
	Cyclization
	Stereoselectivity
Issue Date:	6-May-2022
Publisher:	American Chemical Society
Journal Title:	Journal of the American Chemical Society
Volume:	144
Issue:	19
Start Page:	8460
End Page:	8466
Publisher DOI:	10.1021/jacs.2c02216
Abstract:	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.
Type:	article
URI:	http://hdl.handle.net/2115/86369
Appears in Collections:	化学反応創成研究拠点：ICReDD (Institute for Chemical Reaction Design and Discovery : ICReDD) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)

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