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Asymmetric Alkylation of N-Pivaloyl-o-benzylaniline.

✍ Scribed by James A. Wilkinson; Steven B. Rossington; Sylvie Ducki; John Leonard; Nigel Hussain

Publisher
John Wiley and Sons
Year
2005
Weight
21 KB
Volume
36
Category
Article
ISSN
0931-7597

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✦ Synopsis

Polyphenylalkane derivatives Q 0720

Asymmetric Alkylation of N-Pivaloyl-o-benzylaniline. -Using sBuLi and (-)-sparteine, excellent yields and up to 76% e.e. in favor of the (S)-enantiomer are obtained by alkylation of compound (I) with alkyl halides or a tosylate. The use of (+)-sparteine surrogate DAT gives the opposite sense of asymmetric induction at 80% e.e. for product (IIIa). -(WILKINSON*,

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