Campus Units

Chemistry

Document Type

Article

Publication Version

Published Version

Publication Date

2016

Journal or Book Title

Organic Chemistry Frontiers

Volume

3

Issue

3

First Page

339

Last Page

343

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).

Comments

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.

Creative Commons License

Creative Commons Attribution 3.0 License
This work is licensed under a Creative Commons Attribution 3.0 License.

Copyright Owner

the Partner Organisations

Language

en

File Format

application/pdf

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