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Metal‐Catalyzed Ring‐Opening of Alkylidenecyclopropanes: New Access to Building Blocks with an Acyclic Quaternary Stereogenic Center
Author(s) -
Simaan Samah,
F. G. Goldberg Alexander,
Rosset Stephane,
Marek Ilan
Publication year - 2010
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.200902656
Subject(s) - stereocenter , ring (chemistry) , regioselectivity , center (category theory) , computer science , combinatorial chemistry , stereochemistry , chemistry , catalysis , organic chemistry , enantioselective synthesis , crystallography
Open sesame! A selective metal‐catalyzed ring opening of alkylidenecyclopropane derivatives leads to various functionalized acyclic derivatives possessing challenging quaternary stereocenters. The key feature of this transformation is that the ring opening is faster than the reductive elimination and is highly regioselective; a single ring‐opened product was always observed and the stereointegrity of the quaternary stereogenic center remains unaffected in the process.