Dinuclear zinc synergistic catalytic asymmetric phospha-Michael/Michael cascade reaction: synthesis of 1,2,3-trisubstituted indanes bearing phosphoryl groups

Literature Information

Publication Date 2019-04-03
DOI 10.1039/C9OB00544G
Impact Factor 3.876
Authors

Bing-Kai Tao, Hua Yang, Yuan-Zhao Hua, Min-Can Wang


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Abstract

A new dinuclear zinc synergistic catalytic asymmetric phospha-Michael/Michael cascade reaction of o-dienones and dialkyl phosphates is reported. This method has been proven to be general and efficient for the formation of a range of chiral 1,2,3-trisubstituted indane compounds containing phosphorus groups in good yields (up to 92%) with excellent stereoselectivities (up to >99% ee and up to >99 : 1 dr). The relative configuration of the product was identified as having a trans,trans substitution pattern via two-dimensional (2D) nuclear Overhauser effect spectroscopy 1H–1H NMR experiments. A possible mechanism was proposed.

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Organic & Biomolecular Chemistry

Organic & Biomolecular Chemistry
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Organic & Biomolecular Chemistry (OBC) publishes original and high impact research and reviews in organic chemistry. We welcome research that shows new or significantly improved protocols or methodologies in total synthesis, synthetic methodology or physical and theoretical organic chemistry as well as research that shows a significant advance in the organic chemistry or molecular design aspects of chemical biology, catalysis, supramolecular and macromolecular chemistry, theoretical chemistry, mechanism-oriented physical organic chemistry, medicinal chemistry or natural products. Articles published in the journal should report new work which makes a highly-significant impact in the field. Routine and incremental work is generally not suitable for publication in the journal. More details about key areas of our scope are below. In all cases authors should include in their article clear rationale for why their research has been carried out.

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