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Enantioselective synthesis of pyrroloindolines by a formal [3 + 2] cycloaddition reaction.

ABSTRACT: (R)-BINOL·SnCl(4) was found to catalyze a formal [3 + 2] cycloaddition reaction between C(3)-substituted indoles and 2-amidoacrylates to provide pyrroloindolines. A variety of pyrroloindolines were prepared with high enantioselectivity in one step from simple precursors. This methodology is expected to facilitate the total synthesis of pyrroloindoline alkaloids, an important class of biologically active natural products.

SUBMITTER: Repka LM

PROVIDER: S-EPMC3222144 | biostudies-literature | 2010 Oct

REPOSITORIES: biostudies-literature

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Enantioselective synthesis of pyrroloindolines by a formal [3 + 2] cycloaddition reaction.

Repka Lindsay M LM Ni Jane J Reisman Sarah E SE

Journal of the American Chemical Society 20101001 41

(R)-BINOL·SnCl(4) was found to catalyze a formal [3 + 2] cycloaddition reaction between C(3)-substituted indoles and 2-amidoacrylates to provide pyrroloindolines. A variety of pyrroloindolines were prepared with high enantioselectivity in one step from simple precursors. This methodology is expected to facilitate the total synthesis of pyrroloindoline alkaloids, an important class of biologically active natural products. ...[more]

PMID: 20873714

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