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An Efficient Synthetic Method to Non-Natural α- and β-Tryptophan Analogues via Friedel—Crafts Alkylation of Indoles with Nitroacrylates.

✍ Scribed by Yong Sui; Li Liu; Dong Wang; Yong-Jun Chen

Publisher
John Wiley and Sons
Year
2007
Weight
35 KB
Volume
38
Category
Article
ISSN
0931-7597

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## Abstract The Friedel‐Crafts alkylation of indoles with nitroacrylates could provide __α__‐ and __β__‐tryptophan nitro‐precursors, respectively, in moderate to good yields under Lewis acid catalysis. The diastereoselectivities of the reaction were enhanced by using 2‐substituted indoles. The alky

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## Abstract magnified image The Lewis base‐Lewis base bifunctional catalytic system has been developed and successfully applied to the asymmetric Friedel–Crafts alkylation of indoles with α,β‐unsaturated aldehydes. The reactions are promoted by chiral diphenylprolinol trimethylsilyl ether in the p