Journal
ORGANIC LETTERS
Volume 18, Issue 4, Pages 688-691Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.5b03663
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Funding
- Ministry of Science and Technology of the Republic of China [MOST 103-2113-M-003-009-MY3]
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An unprecedented organocatalytic enantio-selective vinylogous Michael addition/Henry cyclization cascade is presented for the synthesis of highly substituted tetrahydrofluoren-9-ones 3 employing novel 1,3-indandione-derived pronucleophiles 1a-g and nitroalkenes 2. Following very simple protocol, a wide range of products were obtained in good to excellent yields and with excellent enantioinduction (43-98% yield, up to 98% ee). The reaction proceeded with excellent diastereocontrol despite the simultaneous generation of four stereogenic centers. Surprisingly, when 2-(1-phenylethylidene)-1H-indandione (1h) was used as a pronucleophile, no cyclization was observed; and only Michael addition adducts 4a-x were furnished in very good yields and excellent enantioselectivities.
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