Lapierre, AJB and Geib, SJ and Curran, DP
(2007)
Low-temperature Heck reactions of axially chiral o-iodoacrylanilides occur with chirality transfer: Implications for catalytic asymmetric Heck reactions.
Journal of the American Chemical Society, 129 (3).
494 - 495.
ISSN 0002-7863
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Abstract
Low-temperature Heck reactions of chiral o-iodoacrylanilides with achiral palladium catalysts occur with efficient transfer of chirality from the chiral axis of the precursor to the new stereocenter of the product. The results suggest that the primary stereocontrolling step in asymmetric Heck reactions is a dynamic kinetic resolution (oxidative addition to the C-I) bond and not a face selective reaction (complexation or insertion to the alkene). Copyright © 2007 American Chemical Society.
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Details
Item Type: |
Article
|
Status: |
Published |
Creators/Authors: |
|
Date: |
24 January 2007 |
Date Type: |
Publication |
Journal or Publication Title: |
Journal of the American Chemical Society |
Volume: |
129 |
Number: |
3 |
Page Range: |
494 - 495 |
DOI or Unique Handle: |
10.1021/ja067790i |
Schools and Programs: |
Dietrich School of Arts and Sciences > Chemistry |
Refereed: |
Yes |
ISSN: |
0002-7863 |
MeSH Headings: |
Acrylates--chemical synthesis; Alkaloids--chemical synthesis; Anilides--chemical synthesis; Catalysis; Cold Temperature; Cyclization; Heterocyclic Compounds--chemical synthesis; Models, Chemical; Palladium--chemistry; Stereoisomerism |
PubMed ID: |
17227004 |
Date Deposited: |
30 Apr 2013 21:02 |
Last Modified: |
02 Feb 2019 15:58 |
URI: |
http://d-scholarship-dev.library.pitt.edu/id/eprint/18568 |
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