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Literature DB >> 23822901

Highly Z-selective and enantioselective ring-opening/cross-metathesis catalyzed by a resolved stereogenic-at-Ru complex.

Abstract

The synthesis of a ruthenium complex that catalyzes Z-selective (up to 98% Z) asymmetric ring-opening/cross-metathesis with high enantioselectivity (up to 95% ee) is reported. The synthesis of the catalyst features the resolution of a chelating N-heterocyclic carbene complex by ligand substitution with a chiral carboxylate.

Entities: Chemical Disease Species

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Year: 2013 PMID： 23822901 PMCID： PMC3826570 DOI： 10.1021/ja4046422

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

26 in total

1. An enantiomerically pure adamantylimido molybdenum alkylidene complex. An effective new catalyst for enantioselective olefin metathesis.

Authors: W C Peter Tsang; Jesper A Jernelius; G A Cortez; Gabriel S Weatherhead; Richard R Schrock; Amir H Hoveyda
Journal: J Am Chem Soc Date: 2003-03-05 Impact factor: 15.419

2. Chiral Ru-based complexes for asymmetric olefin metathesis: enhancement of catalyst activity through steric and electronic modifications.

Authors: Joshua J Van Veldhuizen; Dennis G Gillingham; Steven B Garber; Osamu Kataoka; Amir H Hoveyda
Journal: J Am Chem Soc Date: 2003-10-15 Impact factor: 15.419

3. Z-Selectivity in olefin metathesis with chelated Ru catalysts: computational studies of mechanism and selectivity.

Authors: Peng Liu; Xiufang Xu; Xiaofei Dong; Benjamin K Keitz; Myles B Herbert; Robert H Grubbs; K N Houk
Journal: J Am Chem Soc Date: 2012-01-17 Impact factor: 15.419

4. Enol ethers as substrates for efficient Z- and enantioselective ring-opening/cross-metathesis reactions promoted by stereogenic-at-Mo complexes: utility in chemical synthesis and mechanistic attributes.

Authors: Miao Yu; Ismail Ibrahem; Masayuki Hasegawa; Richard R Schrock; Amir H Hoveyda
Journal: J Am Chem Soc Date: 2012-01-24 Impact factor: 15.419

5. A novel ligand for the enantioselective ruthenium-catalyzed olefin metathesis.

Authors: Axel Kannenberg; Daniel Rost; Stefan Eibauer; Sascha Tiede; Siegfried Blechert
Journal: Angew Chem Int Ed Engl Date: 2011-03-28 Impact factor: 15.336

6. Synthesis, isolation, characterization, and reactivity of high-energy stereogenic-at-Ru carbenes: stereochemical inversion through olefin metathesis and other pathways.

Authors: R Kashif M Khan; Adil R Zhugralin; Sebastian Torker; Robert V O'Brien; Pamela J Lombardi; Amir H Hoveyda
Journal: J Am Chem Soc Date: 2012-07-20 Impact factor: 15.419

7. Enantioselective ruthenium-catalyzed ring-closing metathesis.

Authors: T J Seiders; D W Ward; R H Grubbs
Journal: Org Lett Date: 2001-10-04 Impact factor: 6.005

8. Acyclic diene metathesis: a versatile tool for the construction of defined polymer architectures.

Authors: Hatice Mutlu; Lucas Montero de Espinosa; Michael A R Meier
Journal: Chem Soc Rev Date: 2010-10-13 Impact factor: 54.564

Review 9. Catalytic enantioselective olefin metathesis in natural product synthesis. Chiral metal-based complexes that deliver high enantioselectivity and more.

Authors: Amir H Hoveyda; Steven J Malcolmson; Simon J Meek; Adil R Zhugralin
Journal: Angew Chem Int Ed Engl Date: 2010 Impact factor: 15.336

10. Highly active chiral ruthenium catalysts for asymmetric ring-closing olefin metathesis.

Authors: Timothy W Funk; Jacob M Berlin; Robert H Grubbs
Journal: J Am Chem Soc Date: 2006-02-15 Impact factor: 15.419

17 in total

Review 1. 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

2. Preparation of chiral-at-metal catalysts and their use in asymmetric photoredox chemistry.

Authors: Jiajia Ma; Xiao Zhang; Xiaoqiang Huang; Shipeng Luo; Eric Meggers
Journal: Nat Protoc Date: 2018-03-01 Impact factor: 13.491

3. Catalyst-controlled stereoselective olefin metathesis as a principal strategy in multistep synthesis design: a concise route to (+)-neopeltolide.

Authors: Miao Yu; Richard R Schrock; Amir H Hoveyda
Journal: Angew Chem Int Ed Engl Date: 2014-11-06 Impact factor: 15.336

4. Catalytic, enantioselective synthesis of 1,2-anti-diols by asymmetric ring-opening/cross-metathesis.

Authors: John Hartung; Robert H Grubbs
Journal: Angew Chem Int Ed Engl Date: 2014-02-19 Impact factor: 15.336

5. Tandem Z-Selective Cross-Metathesis/Dihydroxylation: Synthesis of anti-1,2-Diols.

Authors: Peter K Dornan; Zachary K Wickens; Robert H Grubbs
Journal: Angew Chem Int Ed Engl Date: 2015-04-27 Impact factor: 15.336

6. An overview of N-heterocyclic carbenes.

Authors: Matthew N Hopkinson; Christian Richter; Michael Schedler; Frank Glorius
Journal: Nature Date: 2014-06-26 Impact factor: 49.962

Review 7. Catalytic enantioselective construction of vicinal quaternary carbon stereocenters.

Authors: Feng Zhou; Lei Zhu; Bo-Wen Pan; Yang Shi; Yun-Lin Liu; Jian Zhou
Journal: Chem Sci Date: 2020-07-28 Impact factor: 9.825

8. General approach to the synthesis of the chlorosulfolipids danicalipin A, mytilipin A, and malhamensilipin A in enantioenriched form.

Authors: Won-jin Chung; Joseph S Carlson; Christopher D Vanderwal
Journal: J Org Chem Date: 2014-02-13 Impact factor: 4.354

9. Evolution of catalytic stereoselective olefin metathesis: from ancillary transformation to purveyor of stereochemical identity.

Authors: Amir H Hoveyda
Journal: J Org Chem Date: 2014-04-10 Impact factor: 4.354

10. Carboxylate-assisted C(sp³)-H activation in olefin metathesis-relevant ruthenium complexes.

Authors: Jeffrey S Cannon; Lufeng Zou; Peng Liu; Yu Lan; Daniel J O'Leary; K N Houk; Robert H Grubbs
Journal: J Am Chem Soc Date: 2014-04-25 Impact factor: 15.419