Nitro-enabled catalytic enantioselective formal umpolung alkenylation of β-ketoesters† †Electronic supplementary information (ESI) available: Experimental details, characterization and analytical data. CCDC 1491357 (4ba). For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c7sc02232h Click here for additional data file. Click here for additional data file. Click here for additional data file.
نویسندگان
چکیده
A formal umpolung strategy is presented for the enantioselective installation of an alkenyl group with a terminal double bond at a tertiary center. This one-pot two-step sequence relies on the unique features of the nitro group, which after inverting the polarity of the alkenylating agent toward the desired bond formation, itself serves as a leaving group. The application of this protocol to cyclic b-ketoesters results in densely functionalized products, bearing an all-carbon quaternary stereocenter including an alkenyl substituent with a terminal double bond, in high yields with excellent enantioselectivities.
منابع مشابه
Carbene catalyzed umpolung of α,β-enals: a reactivity study of diamino dienols vs. azolium enolates, and the characterization of advanced reaction intermediates† †Electronic supplementary information (ESI) available: Experimental procedures, compound characterization data, and X-ray crystallographic data of compounds 4b-Et and 4b-Me. CCDC 1014843 and 1014844. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c5sc01027f Click here for additional data file. Click here for additional data file.
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عنوان ژورنال:
دوره 8 شماره
صفحات -
تاریخ انتشار 2017