Nitro-enabled catalytic enantioselective formal umpolung alkenylation of β-ketoesters
Open Access
- 2 August 2017
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Chemical Science
- Vol. 8 (9) , 6686-6690
Abstract
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 β-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.Keywords
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