Asymmetric Vinylogous Aldol-type Reactions of Aldehydes with Allyl Phosphonate and Sulfone

Two catalytic asymmetric vinylogous aldol-type reactions of aldehydes with allyl phosphonate and allyl sulfone have been uncovered in good to high yields for the first time. The bulky ligand-(R)-DTBM-SEGPHOS-was found to be the key to perfectly control both regio- and enantioselectivities. Transform...

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Bibliographic Details
Published in:iScience 2019-04, Vol.14, p.88-99
Main Authors: Yue, Wen-Jun, Zhang, Cheng-Yuan, Yin, Liang
Format: Article
Language:English
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Summary:Two catalytic asymmetric vinylogous aldol-type reactions of aldehydes with allyl phosphonate and allyl sulfone have been uncovered in good to high yields for the first time. The bulky ligand-(R)-DTBM-SEGPHOS-was found to be the key to perfectly control both regio- and enantioselectivities. Transformations of the vinylogous products (including Horner-Wadsworth-Emmons and Julia olefinations) were successfully realized by virtue of the phosphonate and sulfone moieties. Moreover, the present methodology was successfully applied in the asymmetric synthesis of natural products.
ISSN:2589-0042
2589-0042
DOI:10.1016/j.isci.2019.03.010