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Changes of Stereoselectivity in Diels–Alder Reactions by Hydrophobic Solvent Effects and by β‐Cyclodextrin
Author(s) -
Schneider HansJörg,
Sangwan Naresh K.
Publication year - 1987
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.198708961
Subject(s) - stereoselectivity , chemistry , cyclodextrin , solvent , diels–alder reaction , aqueous solution , solvent effects , organic chemistry , adduct , catalysis
The endo/exo product ratios in Diels–Alder reactions can be changed significantly by use of aqueous solvents. The diastereoselectivity can be described as a quantitative function of solvent‐solvophobicity parameters. In some cases, addition of β‐cyclodextrin effects, even more drastic changes in the endo/exo ratio as well as the formation of chiral Diels–Alder adducts.