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Literature DB >> 26840878

High Trans Kinetic Selectivity in Ruthenium-Based Olefin Cross-Metathesis through Stereoretention.

Adam M Johns¹, Tonia S Ahmed², Bradford W Jackson¹, Robert H Grubbs², Richard L Pederson¹.

Abstract

The first kinetically controlled, highly trans-selective (>98%) olefin cross-metathesis reaction is demonstrated using Ru-based catalysts. Reactions with either trans or cis olefins afford products with highly trans or cis stereochemistry, respectively. This E-selective olefin cross-metathesis is shown to occur between two trans olefins and between a trans olefin and a terminal olefin. Additionally, new stereoretentive catalysts have been synthesized for improved reactivity.

Entities: Chemical

Year: 2016 PMID： 26840878 DOI： 10.1021/acs.orglett.6b00031

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

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Cited

7 in total

1. Synthesis of Linear (Z)-α,β-Unsaturated Esters by Catalytic Cross-Metathesis. The Influence of Acetonitrile.

Authors: Elsie C Yu; Brett M Johnson; Erik M Townsend; Richard R Schrock; Amir H Hoveyda
Journal: Angew Chem Int Ed Engl Date: 2016-10-10 Impact factor: 15.336

Review 2. Recent advances in ruthenium-based olefin metathesis.

Authors: O M Ogba; N C Warner; D J O'Leary; R H Grubbs
Journal: Chem Soc Rev Date: 2018-06-18 Impact factor: 54.564

3. A Highly Efficient Synthesis of Z-Macrocycles Using Stereoretentive, Ruthenium-Based Metathesis Catalysts.

Authors: Tonia S Ahmed; Robert H Grubbs
Journal: Angew Chem Int Ed Engl Date: 2017-07-12 Impact factor: 15.336

4. Dipicolinate Complexes of Oxovanadium(IV) and Dioxovanadium(V) with 2-Phenylpyridine and 4,4'-Dimethoxy-2,2'-bipyridyl as New Precatalysts for Olefin Oligomerization.

Authors: Joanna Drzeżdżon; Marta Pawlak; Barbara Gawdzik; Aleksandra Wypych; Karol Kramkowski; Paweł Kowalczyk; Dagmara Jacewicz
Journal: Materials (Basel) Date: 2022-02-13 Impact factor: 3.623

High Trans Kinetic Selectivity in Ruthenium-Based Olefin Cross-Metathesis through Stereoretention.

1. Synthesis of Linear (Z)-α,β-Unsaturated Esters by Catalytic Cross-Metathesis. The Influence of Acetonitrile.

Review 2. Recent advances in ruthenium-based olefin metathesis.

3. A Highly Efficient Synthesis of Z-Macrocycles Using Stereoretentive, Ruthenium-Based Metathesis Catalysts.

4. Dipicolinate Complexes of Oxovanadium(IV) and Dioxovanadium(V) with 2-Phenylpyridine and 4,4'-Dimethoxy-2,2'-bipyridyl as New Precatalysts for Olefin Oligomerization.

5. Tandem Olefin Metathesis/Oxidative Cyclization: Synthesis of Tetrahydrofuran Diols from Simple Olefins.

6. Kinetically controlled E-selective catalytic olefin metathesis.

7. Using stereoretention for the synthesis of E-macrocycles with ruthenium-based olefin metathesis catalysts.