TY  - JOUR
ID  - pittir19871
UR  - http://d-scholarship-dev.library.pitt.edu/19871/
IS  - 35
A1  - Petit, M
A1  - Geib, SJ
A1  - Curran, DP
Y1  - 2004/08/23/
N2  - 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.
JF  - Tetrahedron
VL  - 60
SN  - 0040-4020
TI  - Asymmetric reactions of axially chiral amides: Use of removable ortho-substituents in radical cyclizations of o-iodoacrylanilides and N-allyl-N-o-iodoacrylamides
SP  - 7543 
AV  - public
EP  -  7552
ER  -