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ChemInform Abstract: The tert-Butyl Sulfoximine Group as an Effective ortho-Director of Lithiation: ortho-Metalated S-(tert-Butyl)-S-phenylsulfoximines.

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

Publisher: John Wiley and Sons
Year: 2010
Weight: 32 KB
Volume: 30
Category: Article
ISSN: 0931-7597
DOI: 10.1002/chin.199920076

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✦ Synopsis

The tert-Butyl Sulfoximine Group as an Effective ortho-Director of Lithiation: ortho-Metalated S-(tert-Butyl)-S-phenylsulfoximines.

-Lithiation of the S-tert-butyl-S-phenylsulfoximines (I) occurs selectively at the ortho-position. Trapping with electrophiles at -78 • C affords the orthosubstituted products (III) and (V). Under the optimized conditions shown, the reaction of benzaldehyde proceeds with modest diastereoselectivity. Interestingly, lithiation of the N-trimethylsilyl derivative (Ia) and warming up results in silyl shift to (VI).

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