Lewis-Acid-Catalyzed Asymmetric Alkynylation of Alkynyl 1,2-Diketones: Controllable Formation of 3(2H)‑Furanones and α‑Hydroxy Ketones

We report the highly regio- and enantioselective alkynylation of alkynyl 1,2-diketones under Lewis acid catalysis, leading to the formation of a series of biologically important 3­(2H)-furanones with high to excellent ee values. Moreover, a slight change of the reaction conditions produces a range o...

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Published inOrganic letters Vol. 22; no. 17; pp. 6948 - 6953
Main Authors Liu, Rui, Yang, Shuang, Chen, Zhizhou, Kong, Xiangwen, Ding, Houqiang, Fang, Xinqiang
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 04.09.2020
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
DOMINO REACTION
HIGHLY ENANTIOSELECTIVE ALKYNYLATION
C-BOND FORMATION
CONSTRUCTION
DIMETHYLZINC-MEDIATED ADDITION
CHEMISTRY
HYPEROLACTONE
ALDEHYDES
UMPOLUNG
STRATEGIES
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Summary:We report the highly regio- and enantioselective alkynylation of alkynyl 1,2-diketones under Lewis acid catalysis, leading to the formation of a series of biologically important 3­(2H)-furanones with high to excellent ee values. Moreover, a slight change of the reaction conditions produces a range of highly functionalized α-hydroxy ketones with a high level of enantioselectivity. A variety of further transformations can be easily achieved, demonstrating the synthetic potential of this protocol.
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.0c02505