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Rhodium(II)‐Catalyzed One‐Pot Four‐Component Synthesis of Functionalized Polyether Macrocycles at High Concentration
Author(s) -
Zeghida Walid,
Besnard Céline,
Lacour Jérôme
Publication year - 2010
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201003559
Subject(s) - rhodium , tetrahydrofuran , yield (engineering) , tetrahydropyran , condensation , chemistry , catalysis , diazo , solvent , combinatorial chemistry , component (thermodynamics) , organic chemistry , ring (chemistry) , materials science , physics , metallurgy , thermodynamics
Against conventional wisdom , the rhodium(II)‐catalyzed nontemplated macrocyclization of four separate components in one reaction vessel became more efficient as the concentration was increased. Thus, α‐diazo‐β‐ketoesters underwent condensation with 1,4‐dioxane, tetrahydrofuran, or tetrahydropyran as the solvent to yield 16‐ to 18‐membered polyether macrocycles in up to 75 % yield (see scheme; R=Me, Et, PhCH 2 CH 2 , allyl, PhCHCH 2 ).