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Low-temperature Heck reactions of axially chiral o-iodoacrylanilides occur with chirality transfer: Implications for catalytic asymmetric Heck reactions

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:
CreatorsEmailPitt UsernameORCID
Lapierre, AJB
Geib, SJgeib@pitt.eduGEIB0000-0002-9160-7857
Curran, DPcurran@pitt.eduCURRAN
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.pitt.edu/id/eprint/18568

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