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Asymmetric radical cyclization reactions of axially chiral N-allyl-o-iodoanilides to form enantioenriched N-acyl dihydroindoles

Curran, DP and Chen, CHT and Geib, SJ and Lapierre, AJB (2004) Asymmetric radical cyclization reactions of axially chiral N-allyl-o-iodoanilides to form enantioenriched N-acyl dihydroindoles. Tetrahedron, 60 (20). 4413 - 4424. ISSN 0040-4020

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Abstract

Radical cyclizations of enantiomerically enriched N-allyl-o-iodoanilides provide N-acyl-3-alkyl-2,3-dihydroindoles in good yields and with good to excellent levels of chirality transfer from the N-Ar axis to the new stereocenter. In competitive cyclizations of N-acryloyl-N-allyl-o-iodoanilides, the addition of an o-methyl group reverses the regioselectivity of the radical cyclization from the acryloyl group to the allyl group. Approximate rate constants for representative radical cyclizations have been measured to provide insight into the origin of these observations. © 2004 Elsevier Ltd. All rights reserved.

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Details

Item Type: Article
Status: Published
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Curran, DPcurran@pitt.eduCURRAN
Chen, CHT
Geib, SJgeib@pitt.eduGEIB0000-0002-9160-7857
Lapierre, AJB
Date: 10 May 2004
Date Type: Publication
Journal or Publication Title: Tetrahedron
Volume: 60
Number: 20
Page Range: 4413 - 4424
DOI or Unique Handle: 10.1016/j.tet.2004.02.064
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 0040-4020
Date Deposited: 30 Oct 2013 16:56
Last Modified: 02 Feb 2019 15:58
URI: http://d-scholarship.pitt.edu/id/eprint/19899

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