Enamine Catalysis in the Synthesis of Chiral Structural Analogues of  gem ‐Bisphosphonates Known To Be Biologically Active | Zendy

Barros Maria Teresa | Zendy; Faísca Phillips Ana Maria | Zendy

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Enamine Catalysis in the Synthesis of Chiral Structural Analogues of gem ‐Bisphosphonates Known To Be Biologically Active

Author(s) -

Barros Maria Teresa,

Faísca Phillips Ana Maria

Publication year - 2008

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.200800170

Subject(s) - chemistry , enamine , pyrrolidine , catalysis , benzoic acid , bisphosphonate , optically active , enantioselective synthesis , organocatalysis , organic chemistry , stereochemistry , combinatorial chemistry , osteoporosis , medicine , endocrinology

The synthesis of chiral γ‐keto bisphosphonates is described. Michael addition of cyclic ketones to vinyl gem ‐bisphosphonate catalyzed by 0.1 mol equiv. ( S )‐(+)‐1‐(2‐pyrrolidinyl)pyrrolidine and benzoic acid gave the products in yields of up to 86 %, dr ( cis / trans ) > 1:99 and ee of up to 99 %. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

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