An Asymmetric Variant of the Bischler–Möhlau Indole Synthesis*

Nishani Thennakoon; Gurpreet Kaur; Jingjing Wang; Paul G. Plieger; Gareth J. Rowlands

doi:10.1071/CH14548

RESEARCH ARTICLE

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An Asymmetric Variant of the Bischler–Möhlau Indole Synthesis*

Nishani Thennakoon ^A , Gurpreet Kaur ^A , Jingjing Wang ^A , Paul G. Plieger ^A and Gareth J. Rowlands ^A ^B

+ Author Affiliations

- Author Affiliations

^A Institute of Fundamental Sciences, Massey University, Private Bag 11 222, Palmerston North 4442, New Zealand.

^B Corresponding author. Email: g.j.rowlands@massey.ac.nz

Australian Journal of Chemistry 68(4) 566-575 https://doi.org/10.1071/CH14548
Submitted: 5 September 2014 Accepted: 9 October 2014 Published: 15 January 2015

Abstract

Enantiomerically enriched planar chiral indoles were prepared by an asymmetric variant of the Bischler–Möhlau synthesis. Cinchonine was used as a ‘traceless’ resolving reagent, allowing the formation of readily separable quaternary ammonium salts that were the key intermediates in the indole synthesis. The condensation of the ammonium salt and various substituted anilines was achieved under microwave irradiation; this reduced reaction times and minimised racemisation. The utility of the indoles was demonstrated by their transformation into monophosphane ligands that were capable of coupling challenging substrates in the Suzuki–Miyaura reaction.

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An Asymmetric Variant of the Bischler–Möhlau Indole Synthesis*

Abstract

References

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