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Combining silver catalysis and organocatalysis: a sequential Michael addition/hydroalkoxylation one-pot approach to annulated coumarins.

Hack D, Chauhan P, Deckers K, Hermann GN, Mertens L, Raabe G, Enders D - Org. Lett. (2014)

Bottom Line: A highly stereoselective one-pot procedure for the synthesis of five-membered annulated hydroxycoumarins has been developed.By merging primary amine catalysis with silver catalysis, a series of functionalized coumarin derivatives were obtained in good yields (up to 91%) and good to excellent enantioselectivities (up to 99% ee) via a Michael addition/hydroalkoxylation reaction.Depending on the substituents on the enynone, the synthesis of annulated six-membered rings is also feasible.

View Article: PubMed Central - PubMed

Affiliation: Institute of Organic Chemistry, RWTH Aachen University , Landoltweg 1, 52074 Aachen, Germany.

ABSTRACT
A highly stereoselective one-pot procedure for the synthesis of five-membered annulated hydroxycoumarins has been developed. By merging primary amine catalysis with silver catalysis, a series of functionalized coumarin derivatives were obtained in good yields (up to 91%) and good to excellent enantioselectivities (up to 99% ee) via a Michael addition/hydroalkoxylation reaction. Depending on the substituents on the enynone, the synthesis of annulated six-membered rings is also feasible.

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Combining silver catalysis and organocatalysis: a sequential Michael addition/hydroalkoxylation one-pot approach to annulated coumarins.

Hack D, Chauhan P, Deckers K, Hermann GN, Mertens L, Raabe G, Enders D - Org. Lett. (2014)

Intended Strategy
© Copyright Policy
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4608575&req=5

sch1: Intended Strategy
Bottom Line: A highly stereoselective one-pot procedure for the synthesis of five-membered annulated hydroxycoumarins has been developed.By merging primary amine catalysis with silver catalysis, a series of functionalized coumarin derivatives were obtained in good yields (up to 91%) and good to excellent enantioselectivities (up to 99% ee) via a Michael addition/hydroalkoxylation reaction.Depending on the substituents on the enynone, the synthesis of annulated six-membered rings is also feasible.

View Article: PubMed Central - PubMed

Affiliation: Institute of Organic Chemistry, RWTH Aachen University , Landoltweg 1, 52074 Aachen, Germany.

ABSTRACT
A highly stereoselective one-pot procedure for the synthesis of five-membered annulated hydroxycoumarins has been developed. By merging primary amine catalysis with silver catalysis, a series of functionalized coumarin derivatives were obtained in good yields (up to 91%) and good to excellent enantioselectivities (up to 99% ee) via a Michael addition/hydroalkoxylation reaction. Depending on the substituents on the enynone, the synthesis of annulated six-membered rings is also feasible.

Show MeSH