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Literature DB >> 16173738

Access to macrocyclic endocyclic and exocyclic allylic alcohols by nickel-catalyzed reductive cyclization of ynals.

Beth Knapp-Reed¹, Gireesh M Mahandru, John Montgomery.

Abstract

Ni-catalyzed reductive macrocyclizations of ynals are reported. Disubstituted alkynes afford either endocyclic or exocyclic allylic alcohols depending on the ligand. Phosphine ligands favor the formation of endocyclic olefins, whereas N-heterocyclic carbene ligands favor the formation of exocyclic olefins. Terminal alkynes provide 1,2-disubstituted olefins with N-heterocyclic carbene ligands.

Entities: Chemical Disease

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Year: 2005 PMID： 16173738 DOI： 10.1021/ja054590i

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

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Cited

21 in total

1. Formation of C-C Bonds via Catalytic Hydrogenation and Transfer Hydrogenation: Vinylation, Allylation, and Enolate Addition of Carbonyl Compounds and Imines.

Authors: Ryan L Patman; John F Bower; In Su Kim; Michael J Krische
Journal: Aldrichimica Acta Date: 2008 Impact factor: 3.667

2. 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

3. New N-heterocyclic carbene ligand and its application in asymmetric nickel-catalyzed aldehyde/alkyne reductive couplings.

Authors: Mani Raj Chaulagain; Grant J Sormunen; John Montgomery
Journal: J Am Chem Soc Date: 2007-07-12 Impact factor: 15.419

Review 4. Catalytic carbonyl addition through transfer hydrogenation: a departure from preformed organometallic reagents.

Authors: John F Bower; In Su Kim; Ryan L Patman; Michael J Krische
Journal: Angew Chem Int Ed Engl Date: 2009 Impact factor: 15.336

10. Direct vinylation of alcohols or aldehydes employing alkynes as vinyl donors: a ruthenium catalyzed C-C bond-forming transfer hydrogenation.

Authors: Ryan L Patman; Mani Raj Chaulagain; Vanessa M Williams; Michael J Krische
Journal: J Am Chem Soc Date: 2009-02-18 Impact factor: 15.419

Access to macrocyclic endocyclic and exocyclic allylic alcohols by nickel-catalyzed reductive cyclization of ynals.

1. Formation of C-C Bonds via Catalytic Hydrogenation and Transfer Hydrogenation: Vinylation, Allylation, and Enolate Addition of Carbonyl Compounds and Imines.

2. 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.

3. New N-heterocyclic carbene ligand and its application in asymmetric nickel-catalyzed aldehyde/alkyne reductive couplings.

Review 4. Catalytic carbonyl addition through transfer hydrogenation: a departure from preformed organometallic reagents.

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

6. Nickel-Catalyzed Regiodivergent Approach to Macrolide Motifs.

7. Development of a flexible strategy towards FR900482 and the mitomycins.

8. Nickel-catalyzed coupling of alkenes, aldehydes, and silyl triflates.

9. Exo-selective reductive macrocyclization of ynals.

10. Direct vinylation of alcohols or aldehydes employing alkynes as vinyl donors: a ruthenium catalyzed C-C bond-forming transfer hydrogenation.