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Enantioselective [1,2] Wittig Rearrangement Using an External Chiral Ligand
Author(s) -
Tomooka Katsuhiko,
Yamamoto Kyoko,
Nakai Takeshi
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(19991216)38:24<3741::aid-anie3741>3.0.co;2-5
Subject(s) - enantioselective synthesis , wittig reaction , ligand (biochemistry) , chemistry , stereochemistry , catalysis , carroll rearrangement , organic chemistry , sigmatropic reaction , receptor , biochemistry
Even with only a catalytic amount of chiral bis(dihydrooxazole) 1 as external ligand, the rearrangement of benzyl ethers to alcohols [Eq. (1)] proceeds with high enantioselectivity (over 60 % ee ). This reaction represents the first example of an enantioselective [1,2] Wittig rearrangement.