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External chiral ligand-induced enantioselective versions of the [2,3]-Wittig sigmatropic rearrangement
Katsuhiko Tomooka,
Nobuyuki Komine,
Takeshi Nakai,
Katsuhiko Tomooka
Department of Chemical Technology, Tokyo Institute of Technology, Tokyo, Japan
Search for more papers by this authorNobuyuki Komine
Department of Chemical Technology, Tokyo Institute of Technology, Tokyo, Japan
Search for more papers by this authorCorresponding Author
Takeshi Nakai
Department of Chemical Technology, Tokyo Institute of Technology, Tokyo, Japan
Department of Chemical Technology, Tokyo Institute of Technology, Meguro-ku, Tokyo 152-8552, JapanSearch for more papers by this authorKatsuhiko Tomooka,
Nobuyuki Komine,
Takeshi Nakai,
Katsuhiko Tomooka
Department of Chemical Technology, Tokyo Institute of Technology, Tokyo, Japan
Search for more papers by this authorNobuyuki Komine
Department of Chemical Technology, Tokyo Institute of Technology, Tokyo, Japan
Search for more papers by this authorCorresponding Author
Takeshi Nakai
Department of Chemical Technology, Tokyo Institute of Technology, Tokyo, Japan
Department of Chemical Technology, Tokyo Institute of Technology, Meguro-ku, Tokyo 152-8552, JapanSearch for more papers by this authorFirst published: 19 May 2000
Citations: 30
Abstract
The external chiral ligand-induced enantioselective [2,3]-Wittig rearrangements of crotyl benzyl ethers and crotyl propargylic ethers are described. The most notable is that treatment of (E)-crotyl propargylic ethers with a t-butyllithium/(S;S)-bis(oxazoline) complex provides a relatively high enantioselectivity (up to 89% ee), together with a high threo-diastereoselectivity. Furthermore, examples of the “asymmetric catalytic version” of the rearrangement of crotyl benzyl ethers are presented. Chirality 12:505–509, 2000. © 2000 Wiley-Liss, Inc.
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10.1002/(SICI)1521-3773(19991216)38:24<3741::AID-ANIE3741>3.0.CO;2-5 CAS PubMed Web of Science® Google Scholar
