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A Stable and Recoverable Chiral Ru Lewis Acid: Synthesis, Asymmetric Diels–Alder Catalysis and Structure of the Lewis Acid Methacrolein Complex
Author(s) -
Kündig E. Peter,
Saudan Christophe M.,
Bernardinelli Gérald
Publication year - 1999
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/(sici)1521-3773(19990503)38:9<1219::aid-anie1219>3.0.co;2-d
Subject(s) - methacrolein , lewis acids and bases , chemistry , catalysis , diels–alder reaction , chiral lewis acid , medicinal chemistry , lewis acid catalysis , organic chemistry , stereochemistry , polymer , copolymer , methacrylic acid
Ease of generation , stablity in solution at ambient temperature, high enantioselectivity in Diels–Alder reactions, efficient catalyst recovery, and large rate differences on variation of the anion are all characteristics of the new Ru Lewis acid [CpRu(( S,S )‐biphop‐F)] + (biphop‐F=(C 6 F 5 ) 2 POCH 2 (Ph)CH 2 (Ph)OP(C 6 F 5 ) 2 ). The structure of complex 1 (L=methacrolein, Y=SbF 6 ) provides evidence for a cooperative binding of the dienophile by both the Lewis acid and the anion.