Journal
ORGANIC LETTERS
Volume 21, Issue 17, Pages 7143-7148Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.9b02714
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Funding
- National Natural Science Foundation of China [NSFC 21672170, 21602172, 21203148]
- Natural Science Basic Research Plan in Shaanxi Province of China [2018JC-020, 2018JM2029]
- China Postdoctoral Science Foundation [2018M643705]
- Fundamental Research Funds for the Central Universities
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Asymmetric Prins cyclization of in situ generated quinone methides and o-aminobenzaldehyde has been developed with chiral phosphoric acid as an efficient catalyst. This unconventional method provides a facile access to diverse functionalized trans-fused pyrano-/furo-tetrahydroquinoline derivatives in excellent yield and with excellent diastereo- and enantioselectivities (up to 99% yield and 99% ee). Mechanistic studies suggested that the three adjacent tertiary stereocenters were constructed through the sequential formation of C-O, C-C, and C-N bonds.
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