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Article
Enantioselective dearomative [3 + 2] cycloadditions of indoles with azomethine ylides derived from alanine imino esters
Organic Chemistry Frontiers
Document Type
Article
Disciplines
Publication Version
Published Version
Publication Date
1-1-2016
DOI
10.1039/C5QO00346F
Abstract
Catalytic, enantioselective [3 + 2] cycloadditions of azomethine ylides derived from alanine imino esters with 3-nitroindoles are reported. The dearomative cycloaddition reactions occur in the presence of a catalyst generated in situfrom Cu(OTf)2 and (R)-Difluorphos to form exo′-pyrroloindoline cycloadducts and establish four contiguous stereogenic centers, two of which are fully substituted. The exo′-pyrroloindoline products are formed in moderate-to-good yields (39–85%) with high diastereoselectivities (up to 98:1:1 dr) and enantioselectivities (up to 96% ee).
Creative Commons License
Creative Commons Attribution 3.0
Copyright Owner
the Partner Organisations
Copyright Date
2016
Language
en
File Format
application/pdf
Citation Information
Anthony L. Gerten and Levi M. Stanley. "Enantioselective dearomative [3 + 2] cycloadditions of indoles with azomethine ylides derived from alanine imino esters" Organic Chemistry Frontiers Vol. 3 Iss. 3 (2016) p. 339 - 343 Available at: http://works.bepress.com/levi_stanley/20/
This article is published as Gerten, Anthony L., and Levi M. Stanley. "Enantioselective dearomative [3+ 2] cycloadditions of indoles with azomethine ylides derived from alanine imino esters." Organic Chemistry Frontiers 3, no. 3 (2016): 339-343. doi: 10.1039/C5QO00346F. Posted with permission.