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. 2013 Jun 24:9:1210-6.
doi: 10.3762/bjoc.9.137. Print 2013.

Catalytic asymmetric tandem Friedel-Crafts alkylation/Michael addition reaction for the synthesis of highly functionalized chromans

Jiahuan Peng  1 , Da-Ming Du
Affiliations

Catalytic asymmetric tandem Friedel-Crafts alkylation/Michael addition reaction for the synthesis of highly functionalized chromans

Jiahuan Peng et al. Beilstein J Org Chem. .

Abstract

The enantioselective tandem Friedel-Crafts alkylation/Michael addition reaction of indoles with nitroolefin enoates catalyzed by a diphenylamine-linked bis(oxazoline)-Zn(OTf)2 complex was investigated. This tandem reaction afforded functionalized chiral chromans in good yields with moderate to high stereoselectivities (up to 95:5 dr, up to 99% ee).

Keywords: Friedel–Crafts alkylation; asymmetric catalysis; bis(oxazoline); chroman; tandem reaction.

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Figures

Figure 1
Figure 1
Diphenylamine-linked bis(oxazoline).
Figure 2
Figure 2
X-ray crystal structure of the major diastereomer of 3g (one symmetric molecule and two solvent molecules are not labeled for clarity).
Scheme 1
Scheme 1
The transformation of Friedel–Crafts alkylation product 4a to cycloadduct 3a.
See this image and copyright information in PMC

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