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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
Abstract 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)