Organocatalytic atroposelective synthesis of axially chiral styrenes

Sheng-Cai Zheng, San Wu, Qinghai Zhou, Lung Wa Chung, Liu Ye and Bin Tan ()
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Sheng-Cai Zheng: South University of Science and Technology of China
San Wu: South University of Science and Technology of China
Qinghai Zhou: South University of Science and Technology of China
Lung Wa Chung: South University of Science and Technology of China
Liu Ye: South University of Science and Technology of China
Bin Tan: South University of Science and Technology of China

Nature Communications, 2017, vol. 8, issue 1, 1-9

Abstract: Abstract Axially chiral compounds are widespread in biologically active compounds and are useful chiral ligands or organocatalysts in asymmetric catalysis. It is well-known that styrenes are one of the most abundant and principal feedstocks and thus represent excellent prospective building blocks for chemical synthesis. Driven by the development of atroposelective synthesis of axially chiral styrene derivatives, we discovered herein the asymmetric organocatalytic approach via direct Michael addition reaction of substituted diones/ketone esters/malononitrile to alkynals. The axially chiral styrene compounds were produced with good chemical yields, enantioselectivities and almost complete E/Z-selectivities through a secondary amine-catalysed iminium activation strategy under mild conditions. Such structural motifs are important precursors for further transformations into biologically active compounds and synthetic useful intermediates and may have potential applications in asymmetric synthesis as olefin ligands or organocatalysts.

Date: 2017
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DOI: 10.1038/ncomms15238

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