Catalytic asymmetric inverse-electron-demand aza-Diels-Alder reaction of 1,3-diazadienes with 3-vinylindoles

A facile chiral phosphoric-acid catalyzed asymmetric inverse-electron-demand aza-Diels-Alder reaction of 1,3-diazadienes with 3-vinylindoles was established. By using this mild and practical protocol, a broad range of benzothiazolopyrimidines with three contiguous stereogenic centers were prepared i...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2022-07, Vol.58 (54), p.7515-7518
Main Authors: Miao, Yu-Hang, Hua, Yuan-Zhao, Gao, Hao-Jie, Mo, Nan-Nan, Wang, Min-Can, Mei, Guang-Jian
Format: Article
Language:English
Subjects:
Asymmetry
Diels-Alder reactions
Enantiomers
Hydrogen bonding
Stereoselectivity
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Summary:A facile chiral phosphoric-acid catalyzed asymmetric inverse-electron-demand aza-Diels-Alder reaction of 1,3-diazadienes with 3-vinylindoles was established. By using this mild and practical protocol, a broad range of benzothiazolopyrimidines with three contiguous stereogenic centers were prepared in good yields and excellent diastereo- and enantio-selectivities (43 examples, up to 83% yield, >99% ee and all >20 : 1 dr). A plausible concerted reaction pathway enabled by the dual hydrogen-bonding effect was proposed to account for the observed excellent enantioselectivity and specific trans - trans diastereoselectivity. A facile chiral phosphoric-acid catalyzed asymmetric inverse-electron-demand aza-Diels-Alder reaction of 1,3-diazadienes with 3-vinylindoles was established.
ISSN:1359-7345
1364-548X
DOI:10.1039/d2cc02458f