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.
Original language | English (US) |
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Pages (from-to) | 6686-6690 |
Number of pages | 5 |
Journal | Chemical Science |
Volume | 8 |
Issue number | 9 |
DOIs | |
State | Published - 2017 |
Externally published | Yes |
ASJC Scopus subject areas
- General Chemistry