Enantioselective dearomative [3 + 2] cycloadditions of indoles with azomethine ylides derived from alanine imino esters
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The Department of Chemistry seeks to provide students with a foundation in the fundamentals and application of chemical theories and processes of the lab. Thus prepared they me pursue careers as teachers, industry supervisors, or research chemists in a variety of domains (governmental, academic, etc).
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The Department of Chemistry was founded in 1880.
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1880-present
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- College of Liberal Arts and Sciences (parent college)
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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).
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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.