Journal
ORGANIC LETTERS
Volume 23, Issue 7, Pages 2471-2476Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c00392
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Funding
- National Key Research and Development Program of China [2017YFB0307200]
- Zhejiang Key Laboratory of Green Pesticides and Cleaner Production Technology
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A new method has been developed for the selective construction of enantioenriched eight-membered cyclic ethers by combining squaramide and DBU catalysis. The reaction yields a variety of eight-membered cyclic ethers with high stereoselectivity, showcasing the practicality of ynones as C4-syntons for synthesizing chiral medium-membered rings.
A sequential enantioselective conjugate addition/hydroalkoxylation between in situ generated ortho-quinomethanes and ynones by combining bifunctional squaramide and DBU catalysis has been developed. A variety of eight-membered cyclic ethers with two contiguous tertiary stereocenters were obtained in high yields with excellent stereoselectivities. This reaction not only provides a new strategy for constructing enantioenriched eight-membered cyclic ethers but also demonstrates the practicability of ynones as C4-syntons for the synthesis of chiral medium-membered rings.
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