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Organic letters
Dec 16, 2011;13 (24): 6596-9.

Ethylene in organic synthesis: a new route to anticholenergic pyrrolidinoindolines, and other molecules with all carbon-quaternary centers via asymmetric hydrovinylation.

Hwan Jung Lim, T V RajanBabu
Author Information
  1. Hwan Jung Lim: Department of Chemistry, The Ohio State University, 100 West 18th Avenue, Columbus, Ohio 43210, USA.
PMID: 22103775 DOI: 10.1021/ol203052y

Abstract

The asymmetric hydrovinylation (1 mol % Ni-cat., 1 atm, ethylene, >98% ee) products from 1-methylenetetralines are readily converted into 3,3-disubstituted oxindoles and subsequently to pyrrolidinoindolines. These hydrovinylation products are also useful for the syntheses of enantiopure benzomorphans.

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Grants

  1. R01 GM075107/NIGMS NIH HHS
  2. R01 GM075107-04/NIGMS NIH HHS

MeSH Term

Catalysis
Ethylenes
Indoles
Molecular Structure
Oxindoles
Pyrrolidines
Stereoisomerism

Chemicals

Ethylenes
Indoles
Oxindoles
Pyrrolidines
2-oxindole
ethylene
Journal Article Research Support, N.I.H., Extramural

Word Cloud

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