Premium
External chiral ligand‐induced enantioselective versions of the [2,3]‐Wittig sigmatropic rearrangement
Author(s) -
Tomooka Katsuhiko,
Komine Nobuyuki,
Nakai Takeshi
Publication year - 2000
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/(sici)1520-636x(2000)12:5/6<505::aid-chir36>3.0.co;2-3
Subject(s) - enantioselective synthesis , chemistry , sigmatropic reaction , oxazoline , stereochemistry , chirality (physics) , ligand (biochemistry) , wittig reaction , catalysis , organic chemistry , physics , receptor , chiral anomaly , biochemistry , fermion , quantum mechanics , nambu–jona lasinio model
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.