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Highly Enantioselective Approach to Geminal Bisphosphonates by Organocatalyzed Michael‐Type Addition of β‐Ketoesters
Author(s) -
Capuzzi Marinella,
Perdicchia Dario,
Jørgensen Karl Anker
Publication year - 2007
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200701317
Subject(s) - geminal , enantioselective synthesis , stereocenter , conjugate , michael reaction , adduct , chemistry , optically active , catalysis , organic chemistry , quaternary carbon , combinatorial chemistry , mathematics , mathematical analysis
A valuable organocatalyzed protocol has been developed for the asymmetric synthesis of bisphosphonate derivatives, a class of pharmaceutically important molecules. Cheap and commercially available dihydroquinine effectively catalyzed conjugate additions of cyclic β‐ketoesters to ethylidenebisphosphonate esters, leading to optically active geminal bisphosphonates, bearing an all‐carbon substituted quaternary stereocenter, in high yields and enantioselectivities of up to 99 % ee . Further elaborations of Michael adducts to the corresponding bisphosphonic acids or vinyl phosphonates have also been successfully performed, with conservation of optical purity.