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Asymmetric reactions of axially chiral amides: Use of removable ortho-substituents in radical cyclizations of o-iodoacrylanilides and N-allyl-N-o-iodoacrylamides

Petit, M and Geib, SJ and Curran, DP (2004) Asymmetric reactions of axially chiral amides: Use of removable ortho-substituents in radical cyclizations of o-iodoacrylanilides and N-allyl-N-o-iodoacrylamides. Tetrahedron, 60 (35). 7543 - 7552. ISSN 0040-4020

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Abstract

Radical cyclizations of enantiomerically enriched o-iodoacrylanilides and N-allyl-o-iodoanilides bearing a removable ortho-substituent such as trimethylsilyl or bromine provide oxindoles and indoles in good yields and with good to excellent levels of chirality transfer from the N-Ar axis to the new stereocenter. Transition state models for the chirality transfer are suggested. Chemoselectivity of the radical cyclization in favor of the iodine in the case of 2-iodo-6-bromo-N-allylacrylamides has been exploited for the synthesis of chiral pyrroloquinolinones by a one-pot sequence of 5-exo and 6-endo cyclizations. © 2004 Elsevier Ltd. All rights reserved.


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Details

Item Type: Article
Status: Published
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Petit, M
Geib, SJgeib@pitt.eduGEIB0000-0002-9160-7857
Curran, DPcurran@pitt.eduCURRAN
Date: 23 August 2004
Date Type: Publication
Journal or Publication Title: Tetrahedron
Volume: 60
Number: 35
Page Range: 7543 - 7552
DOI or Unique Handle: 10.1016/j.tet.2004.05.116
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 0040-4020
Date Deposited: 17 Oct 2013 15:36
Last Modified: 02 Feb 2019 15:58
URI: http://d-scholarship.pitt.edu/id/eprint/19871

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