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Chemically Modified β ‐Cyclodextrins as Supramolecular Carriers in the Biphasic Palladium‐Catalyzed Cleavage of Allylic Carbonates: Activity Enhancement and Substrate‐Selective Catalysis
Author(s) -
Lacroix Thibaut,
Bricout Hervé,
Tilloy Sébastien,
Monflier Eric
Publication year - 1999
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/(sici)1099-0690(199911)1999:11<3127::aid-ejoc3127>3.0.co;2-m
Subject(s) - chemistry , catalysis , palladium , allylic rearrangement , cleavage (geology) , substrate (aquarium) , supramolecular catalysis , supramolecular chemistry , combinatorial chemistry , organic chemistry , crystal structure , oceanography , geology , geotechnical engineering , fracture (geology) , engineering
Catalytic amounts of chemically modified β ‐cyclodextrins allowed us to achieve, in high yields, the deprotection of various water‐insoluble allylic carbonates in a genuine two‐phase system without co‐solvent. The catalytic activities were up to 300 times higher than those observed without modified cyclodextrins. The process of molecular recognition between the cyclodextrin and the substrate allowed us to perform substrate‐selective catalytic reactions which cannot be achieved in homogeneous or biphasic media with conventional transition metal catalysts.