CaltechAUTHORS
  A Caltech Library Service

Catalytic, Enantioselective Synthesis of 1,2-anti-Diols by Asymmetric Ring-Opening/Cross-Metathesis

Hartung, John and Grubbs, Robert H. (2014) Catalytic, Enantioselective Synthesis of 1,2-anti-Diols by Asymmetric Ring-Opening/Cross-Metathesis. Angewandte Chemie International Edition, 53 (15). pp. 3885-3888. ISSN 1433-7851. PMCID PMC4037230. https://resolver.caltech.edu/CaltechAUTHORS:20140224-131355335

[img] PDF - Accepted Version
See Usage Policy.

160Kb
[img]
Preview
PDF - Supplemental Material
See Usage Policy.

4Mb

Use this Persistent URL to link to this item: https://resolver.caltech.edu/CaltechAUTHORS:20140224-131355335

Abstract

An enantioselective method for the synthesis of 1,2-anti-diols has been developed. A cyclometalated chiral-at-ruthenium complex catalyzes the asymmetric ring-opening/cross-metathesis of dioxygenated cyclobutenes, thus resulting in functionally rich synthetic building blocks. Syntheses of the insect pheromone (+)-endo-brevicomin and monosaccharide ribose demonstrate the synthetic utility of the 1,2-anti-diol fragments generated in the title reaction.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1002/anie.201310767DOIArticle
http://onlinelibrary.wiley.com/doi/10.1002/anie.201310767/abstractPublisherArticle
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4037230/PubMed CentralArticle
ORCID:
AuthorORCID
Grubbs, Robert H.0000-0002-0057-7817
Alternate Title:Catalytic, Enantioselective Synthesis of 1,2-anti Diols via Asymmetric Ring Opening/Cross Metathesis
Additional Information:© 2014 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. Received: December 11, 2013; Article first published online: 19 Feb. 2014. This work was financially supported by the NIH (5R01GM031332-27 to R.H.G.) and the NSF (CHE-1048404 to R.H.G.). We thank Materia, Inc. for donation of metathesis catalysts and Dr. Jeffrey Cannon, Dr. Bill Morandi, and Zach K. Wickens for helpful discussion.
Funders:
Funding AgencyGrant Number
NIH5R01GM031332-27
NSFCHE-1048404
Subject Keywords:alcohols; asymmetric catalysis; metathesis; pheromones; ruthenium
Issue or Number:15
PubMed Central ID:PMC4037230
Record Number:CaltechAUTHORS:20140224-131355335
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20140224-131355335
Official Citation:Hartung, J. and Grubbs, R. H. (2014), Catalytic, Enantioselective Synthesis of 1,2-anti-Diols by Asymmetric Ring-Opening/Cross-Metathesis. Angew. Chem. Int. Ed., 53: 3885–3888. doi: 10.1002/anie.201310767
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:43947
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:05 Mar 2014 18:55
Last Modified:03 Oct 2019 06:13

Repository Staff Only: item control page