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The tert-butyl sulfoximine group as an effective ortho-director of lithiation: ortho-metallated S-(tert-butyl)-S-phenylsulfoximines

✍ Scribed by V. Levacher; B.Langer Eriksen; M. Begtrup; G. Dupas; G. Quéguiner; J. Duflos; J. Bourguignon

Publisher: Elsevier Science
Year: 1999
Tongue: French
Weight: 215 KB
Volume: 40
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(99)00060-x

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✦ Synopsis

The readily available S-(tert-butyl)-N-(trimethylsilyl)-S-phenylsulfoximine was prepared from S-methyl-N-(trimethylsilyl)-S-phenylsulfoximine via lithiation-methylation sequences. The reaction with n-butyllithium in THF at -780C afforded the corresponding ortho-lithiated species which could be trapped with different electrophiles in good yields. Addition of benzaldehyde proceeded with a modest diastereoselectivity (de=52%).

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