C-2/C-3 Annulation and C-2 Alkylation of Indoles with 2-Alkoxycyclopropanoate Esters

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C-2/c-3 annulation and C-2 alkylation of indoles with 2-alkoxycyclopropanoate esters.

The annulation reaction between various indoles and 2-alkoxycyclopropanoate esters is reported. Both high efficiency and complete stereochemical control were observed in some cases with this annulation process. A single stereocenter on the cyclopropane controls the diastereoselective formation of up to four new stereocenters. A different reaction course was observed with 3-substituted indole su...

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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 situ from Cu(OTf)2 and (R)-Difluorphos to form exo’-pyrroloindoline cycloadducts and establish four contiguous stereogenic centers, two of which are fully substituted. ...

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ژورنال

عنوان ژورنال: Journal of the American Chemical Society

سال: 2007

ISSN: 0002-7863,1520-5126

DOI: 10.1021/ja067821+