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Literature DB >> 20491487

Direct ruthenium-catalyzed C-C coupling of ethanol: diene hydro-hydroxyethylation to form all-carbon quaternary centers.

Abstract

Under ruthenium-catalyzed transfer hydrogenation conditions, direct C-C coupling of ethanol and 2-substituted dienes occurs to furnish products of hydro-hydroxyethylation: anti-configured neopentyl homoallylic alcohols. Identical adducts are generated from acetaldehyde under related conditions employing isopropanol as reductant.

Entities: Chemical Gene

Mesh：

Substances：

Year: 2010 PMID： 20491487 PMCID： PMC2884076 DOI： 10.1021/ol101077v

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

28 in total

Review 1. Non-metathesis ruthenium-catalyzed C-C bond formation.

Authors: B M Trost; F D Toste; A B Pinkerton
Journal: Chem Rev Date: 2001-07 Impact factor: 60.622

2. Catalytic, enantioselective addition of substituted allylic trichlorosilanes using a rationally-designed 2,2'-bispyrrolidine-based bisphosphoramide.

Authors: S E Denmark; J Fu
Journal: J Am Chem Soc Date: 2001-09-26 Impact factor: 15.419

3. Nickel-Catalyzed Homoallylation of Aldehydes in the Presence of Water and Alcohols We thank Mr. Y. Ohhama, NMR Facility, for his outstanding technical assistance. Financial support from the Ministry of Education, Science, Sports, and Culture, Japanese Government, Grant-in-Aid for Scientific Research B, is acknowledged.

Authors: Masanari Kimura; Akihiro Ezoe; Shuji Tanaka; Yoshinao Tamaru
Journal: Angew Chem Int Ed Engl Date: 2001-10-01 Impact factor: 15.336

4. Direct, catalytic hydroaminoalkylation of unactivated olefins with N-alkyl arylamines.

Authors: Seth B Herzon; John F Hartwig
Journal: J Am Chem Soc Date: 2007-05-03 Impact factor: 15.419

5. A New catalytic C[bond]C bond-forming hydrogenation: reductive coupling of dienes and glyoxals under catalytic hydrogenation conditions.

Authors: Hye-Young Jang; Ryan R Huddleston; Michael J Krische
Journal: Angew Chem Int Ed Engl Date: 2003-09-05 Impact factor: 15.336

6. Regio- and stereoselective nickel-catalyzed homoallylation of aldehydes with 1,3-dienes.

Authors: Masanari Kimura; Akihiro Ezoe; Masahiko Mori; Keisuke Iwata; Yoshinao Tamaru
Journal: J Am Chem Soc Date: 2006-07-05 Impact factor: 15.419

7. Asymmetric reductive coupling of dienes and aldehydes catalyzed by nickel complexes of spiro phosphoramidites: highly enantioselective synthesis of chiral bishomoallylic alcohols.

Authors: Yun Yang; Shou-Fei Zhu; Hai-Feng Duan; Chang-Yue Zhou; Li-Xin Wang; Qi-Lin Zhou
Journal: J Am Chem Soc Date: 2007-02-02 Impact factor: 15.419

8. Nickel-catalyzed intermolecular coupling of 1,3-dienes and aldehydes via transmetalation of nickelacycles with diisobutylaluminum acetylacetonate.

Authors: Yoshihiro Sato; Rieko Sawaki; Nozomi Saito; Miwako Mori
Journal: J Org Chem Date: 2002-02-08 Impact factor: 4.354

9. Nickel-catalyzed enantio- and diastereoselective three-component coupling of 1,3-dienes, aldehydes, and silanes using chiral N-heterocyclic carbenes as ligands.

Authors: Yoshihiro Sato; Yu Hinata; Reiko Seki; Yoshihiro Oonishi; Nozomi Saito
Journal: Org Lett Date: 2007-11-17 Impact factor: 6.005

10. Nickel-catalyzed homoallylation reaction of aldehydes with 1,3-dienes: stereochemical and mechanistic studies.

Authors: Teck-Peng Loh; Hong-Yan Song; Yan Zhou
Journal: Org Lett Date: 2002-08-08 Impact factor: 6.005

17 in total

1. Alkyne-aldehyde reductive C-C coupling through ruthenium-catalyzed transfer hydrogenation: direct regio- and stereoselective carbonyl vinylation to form trisubstituted allylic alcohols in the absence of premetallated reagents.

Authors: Joyce C Leung; Ryan L Patman; Brannon Sam; Michael J Krische
Journal: Chemistry Date: 2011-09-27 Impact factor: 5.236

2. Formation of C-C bonds via ruthenium-catalyzed transfer hydrogenation().

Authors: Joseph Moran; Michael J Krische
Journal: Pure Appl Chem Date: 2012-03-13 Impact factor: 2.453

3. Axial preferences in allylations via the Zimmerman-Traxler transition state.

Authors: Noga Gilboa; Hao Wang; Kendall N Houk; Ilan Marek
Journal: Chemistry Date: 2011-06-03 Impact factor: 5.236

4. Amplification of anti-diastereoselectivity via Curtin-Hammett effects in ruthenium-catalyzed hydrohydroxyalkylation of 1,1-disubstituted allenes: diastereoselective formation of all-carbon quaternary centers.

Authors: Jason R Zbieg; Emma L McInturff; Joyce C Leung; Michael J Krische
Journal: J Am Chem Soc Date: 2010-12-22 Impact factor: 15.419

5. Diastereo- and enantioselective ruthenium-catalyzed hydrohydroxyalkylation of 2-silyl-butadienes: carbonyl syn-crotylation from the alcohol oxidation level.

Authors: Jason R Zbieg; Joseph Moran; Michael J Krische
Journal: J Am Chem Soc Date: 2011-06-16 Impact factor: 15.419

6. Iridium Catalyzed Hydro-hydroxyalkylation of Butadiene: Carbonyl Crotylation.

Authors: Jason R Zbieg; Takeo Fukuzumi; Michael J Krische
Journal: Adv Synth Catal Date: 2010-10-04 Impact factor: 5.837

Review 7. Ruthenium-Catalyzed Transfer Hydrogenation for C-C Bond Formation: Hydrohydroxyalkylation and Hydroaminoalkylation via Reactant Redox Pairs.

Authors: Felix Perez; Susumu Oda; Laina M Geary; Michael J Krische
Journal: Top Curr Chem (Cham) Date: 2016-05-30

Review 8. Axial preferences in allylation reactions via the Zimmerman-Traxler transition state.

Authors: Tom Mejuch; Noga Gilboa; Eric Gayon; Hao Wang; K N Houk; Ilan Marek
Journal: Acc Chem Res Date: 2013-05-14 Impact factor: 22.384

Review 9. Catalytic enantioselective C-H functionalization of alcohols by redox-triggered carbonyl addition: borrowing hydrogen, returning carbon.

Authors: John M Ketcham; Inji Shin; T Patrick Montgomery; Michael J Krische
Journal: Angew Chem Int Ed Engl Date: 2014-07-23 Impact factor: 15.336

10. Direct, redox-neutral prenylation and geranylation of secondary carbinol C-H bonds: C4-regioselectivity in ruthenium-catalyzed C-C couplings of dienes to α-hydroxy esters.

Authors: Joyce C Leung; Laina M Geary; Te-Yu Chen; Jason R Zbieg; Michael J Krische
Journal: J Am Chem Soc Date: 2012-09-17 Impact factor: 15.419