Synthesis of geminal bisphosphonates via organocatalyzed enantioselective Michael additions of cyclic ketones and 4-piperidones

Ana Maria Madeira Martins Faísca Phillips; Maria Teresa Barros

doi:10.1039/c1ob06473h

Synthesis of geminal bisphosphonates via organocatalyzed enantioselective Michael additions of cyclic ketones and 4-piperidones

Ana Maria Madeira Martins Faísca Phillips, Maria Teresa Barros

Research output: Contribution to journal › Article › peer-review

17 Citations (Scopus)

Abstract

A Michael addition reaction of cyclic ketones and piperidones to a vinyl phosphonate is described. The reaction, catalyzed by chiral diamines, produced geminal g-oxobisphosphonates in high yields (up to 92%) and very high ees (up to >99%). Disubstituted ketones gave drs of up to 8 : 92. The synthesis and characterization of several new compounds with potential biological activity is described.

Original language	Unknown
Pages (from-to)	404-412
Journal	Organic & Biomolecular Chemistry
Volume	10
Issue number	2
DOIs	https://doi.org/10.1039/c1ob06473h
Publication status	Published - 1 Jan 2012

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10.1039/c1ob06473h

Cite this

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abstract = "A Michael addition reaction of cyclic ketones and piperidones to a vinyl phosphonate is described. The reaction, catalyzed by chiral diamines, produced geminal g-oxobisphosphonates in high yields (up to 92%) and very high ees (up to >99%). Disubstituted ketones gave drs of up to 8 : 92. The synthesis and characterization of several new compounds with potential biological activity is described.",

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N2 - A Michael addition reaction of cyclic ketones and piperidones to a vinyl phosphonate is described. The reaction, catalyzed by chiral diamines, produced geminal g-oxobisphosphonates in high yields (up to 92%) and very high ees (up to >99%). Disubstituted ketones gave drs of up to 8 : 92. The synthesis and characterization of several new compounds with potential biological activity is described.

AB - A Michael addition reaction of cyclic ketones and piperidones to a vinyl phosphonate is described. The reaction, catalyzed by chiral diamines, produced geminal g-oxobisphosphonates in high yields (up to 92%) and very high ees (up to >99%). Disubstituted ketones gave drs of up to 8 : 92. The synthesis and characterization of several new compounds with potential biological activity is described.

U2 - 10.1039/c1ob06473h

DO - 10.1039/c1ob06473h

M3 - Article

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SN - 1477-0520

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EP - 412

JO - Organic & Biomolecular Chemistry

JF - Organic & Biomolecular Chemistry

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