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External chiral ligand-induced enantioselective versions of the [2,3]-Wittig sigmatropic rearrangement

✍ Scribed by Katsuhiko Tomooka; Nobuyuki Komine; Takeshi Nakai

Publisher: John Wiley and Sons
Year: 2000
Tongue: English
Weight: 144 KB
Volume: 12
Category: Article
ISSN: 0899-0042
DOI: 10.1002/(sici)1520-636x(2000)12:5/6<505::aid-chir36>3.0.co;2-3

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✦ Synopsis

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.

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