eprintid: 19871
rev_number: 16
userid: 1418
dir: disk0/00/01/98/71
datestamp: 2013-10-17 15:36:00
lastmod: 2019-02-02 15:58:43
status_changed: 2013-10-17 15:36:00
type: article
metadata_visibility: show
item_issues_count: 0
eprint_status: archive
creators_name: Petit, M
creators_name: Geib, SJ
creators_name: Curran, DP
creators_email: 
creators_email: geib@pitt.edu
creators_email: curran@pitt.edu
creators_id: 
creators_id: GEIB
creators_id: CURRAN
creators_orcid: 
creators_orcid: 0000-0002-9160-7857
creators_orcid: 
title: Asymmetric reactions of axially chiral amides: Use of removable ortho-substituents in radical cyclizations of o-iodoacrylanilides and N-allyl-N-o-iodoacrylamides
ispublished: pub
divisions: sch_as_chemistry
full_text_status: public
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.
date: 2004-08-23
date_type: published
publication: Tetrahedron
volume: 60
number: 35
pagerange: 7543 - 7552
refereed: TRUE
issn: 0040-4020
id_number: 10.1016/j.tet.2004.05.116
citation:   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     
document_url: http://d-scholarship-dev.library.pitt.edu/19871/1/licence.txt