Addition of alkynes to aldehydes and activated ketones catalyzed by rhodium-phosphine complexes.

Addition of alkynes to aldehydes and activated ketones catalyzed by rhodium-phosphine complexes. Research Abstract Details 

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Addition of alkynes to aldehydes and activated ketones catalyzed by rhodium-phosphine complexes. Abstract Text:

Pawan K Dhondi,Patrick Carberry,Lydia B Choi,John D Chisholm,Pawan K Dhondi,Patrick Carberry,Lydia B Choi,John D Chisholm,Pawan K Dhondi,Patrick Carberry,Lydia B Choi,John D Chisholm,

A mixture of 2-(di-tert-butylphosphino)biphenyl and dicarbonylacetonato rhodium(I) provides an effective catalyst system for the addition of alkynes to aldehydes and activated ketones. In contrast to the more common zinc-catalyzed processes, enolizable 1,2-dicarbonyls are excellent substrates for these rhodium-catalyzed additions. This reaction allows for the formation of propargylic alcohols under mild conditions, tolerating many functional groups (such as carboxylic acids) that are incompatible with other methods. Little selectivity was observed in cases of unsymmetrical 1,2-diketones. Addition of alkynes to aldehydes with an adjacent chirality center usually provides the Felkin addition product with excellent selectivity in some cases. Studies on the catalyst structure show that both the beta-diketonate and a carbon monoxide ligand appear to be bound to the active catalyst. The use of chiral phosphines to induce asymmetry in the propargyl alcohol products provided low enantioselectivity, which may be due to the phosphine having a distal relationship to the reacting centers. Modification of other ligands, such as the beta-diketonate, appears to be a more promising avenue for the development of an enantioselective variant.

Addition of alkynes to aldehydes and activated ketones catalyzed by rhodium-phosphine complexes. Publishing Authors By Initials

PK Dhondi,P Carberry,LB Choi,JD Chisholm,PK Dhondi,P Carberry,LB Choi,JD Chisholm,PK Dhondi,P Carberry,LB Choi,JD Chisholm,

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Addition of alkynes to aldehydes and activated ketones catalyzed by rhodium-phosphine complexes. Journal Published:

PUBLICATION TYPE: Journal Article

Journal: The Journal of organic chemistry

VOLUME: 72

Page Numbers: 9590-6

Journal Abbreviation: J. Org. Chem.

ISSN: 0022-3263

DAY: 14

MONTH: 11

YEAR: 2007

Addition of alkynes to aldehydes and activated ketones catalyzed by rhodium-phosphine complexes. Information

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LANGUAGE: eng

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Grant and Affiliation Information for Addition of alkynes to aldehydes and activated ketones catalyzed by rhodium-phosphine complexes.

AFFILIATION: Department of Chemistry, 1-014 Center for Science and Technology, Syracuse University, Syracuse, New York 13244.

Country: United States

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MEDLINETA: J Org Chem

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