Catalytic and asymmetric Friedel–Crafts alkylation of indoles with nitroacrylates. Application to the synthesis of tryptophan analogues
TetrahedronPublished 25 April 2007
Yong Sui, Li Liu, Junling Zhao, Dong Wang, Xiaopeng Cheng
Citations66
SJR quartileQ3
SJR score0.43
SNIP0.60
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TL;DR
An asymmetric Friedel–Crafts alkylation of indoles with nitroacrylates catalyzed by chiral (4R,5S)-DiPh-BOX (L1)–Cu(OTf)2 complex (10 mol %) has been developed and could be easily reduced to optically active tryptophan analogues with Zn/H+.
Abstract
An asymmetric Friedel–Crafts alkylation of indoles with nitroacrylates catalyzed by chiral (4R,5S)-DiPh-BOX (L1)–Cu(OTf)2 complex (10 mol %) has been developed. The reactions provide tryptophan nitro-precursors in moderate diastereoselectivities (anti/syn up to 72:28) and good to excellent enantioselectivities (up to 99% ee). The alkylation products could be easily reduced to optically active tryptophan analogues with Zn/H+.
Keywords
Chemistry
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