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Heterogeneous Reductive Isomerization Reaction Using Catalytic Pd/C and H_2

Caspi, Daniel D. and Garg, Neil K. and Stoltz, Brian M. (2005) Heterogeneous Reductive Isomerization Reaction Using Catalytic Pd/C and H_2. Organic Letters, 7 (12). pp. 2513-2516. ISSN 1523-7060. https://resolver.caltech.edu/CaltechAUTHORS:20170222-150113004

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Abstract

A highly selective catalytic reductive isomerization reaction is described. The extremely mild and neutral reaction conditions (10% Pd/C, H_2, and MeOH at 0 °C) tolerate a wide range of functional groups and generally result in excellent yields. Mechanistic studies suggest that this reaction does not proceed via a stepwise reduction/elimination sequence or a π-allylpalladium intermediate.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/ol050952fDOIArticle
http://pubs.acs.org/doi/abs/10.1021/ol050952fPublisherArticle
http://pubs.acs.org/doi/suppl/10.1021/ol050952fRelated ItemSupporting Information
ORCID:
AuthorORCID
Stoltz, Brian M.0000-0001-9837-1528
Additional Information:© 2005 American Chemical Society. Received 28 April 2005. Published online 14 May 2005. Published in print 1 June 2005. The authors gratefully acknowledge the NIH-NIGMS (R01 GM65961-01), the NDSEG (predoctoral fellowship to N.K.G.), Eli Lilly (predoctoral fellowship to D.D.C.), AstraZeneca, Boehringer Ingelheim, Johnson & Johnson, Pfizer, Merck, Amgen, Research Corporation, Roche, and GlaxoSmithKline for generous funding.
Funders:
Funding AgencyGrant Number
NIHR01GM65961-01
National Defense Science and Engineering Graduate (NDSEG) FellowshipUNSPECIFIED
Eli LillyUNSPECIFIED
AstraZenecaUNSPECIFIED
Boehringer-IngelheimUNSPECIFIED
Johnson and JohnsonUNSPECIFIED
PfizerUNSPECIFIED
MerckUNSPECIFIED
AmgenUNSPECIFIED
Research CorporationUNSPECIFIED
RocheUNSPECIFIED
GlaxoSmithKlineUNSPECIFIED
Issue or Number:12
Record Number:CaltechAUTHORS:20170222-150113004
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20170222-150113004
Official Citation:Heterogeneous Reductive Isomerization Reaction Using Catalytic Pd/C and H2 Daniel D. Caspi, Neil K. Garg, and Brian M. Stoltz Organic Letters 2005 7 (12), 2513-2516 DOI: 10.1021/ol050952f
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:74474
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:23 Feb 2017 17:22
Last Modified:03 Oct 2019 16:39

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