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Dearomative (3+2) cycloadditions of unprotected indoles

Bram Ryckaert (UGent) , Jan Hullaert, Kristof Van Hecke (UGent) and Johan Winne (UGent)
(2022) ORGANIC LETTERS. 24(23). p.4119-4123
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Abstract
The (3 + 2) cycloaddition of various indoles with a dithioallyl cation affords dearomatized cyclopentannulated adducts, with complete control of regioselectivity and excellent chemo- and diastereoselectivity. The success of the reaction critically relies on the use of an excess of very strong Bronsted acid, which paradoxically prevents carbocationic side reactions. The reaction tolerates sensitive functionalities such as basic amines or free hydroxyls, and we demonstrate its use in late stage derivatization of highly functionalized, unprotected indoles.
Keywords
ALLYL CATIONS, CYCLOPENTANOID, CYCLOADDITION

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MLA
Ryckaert, Bram, et al. “Dearomative (3+2) Cycloadditions of Unprotected Indoles.” ORGANIC LETTERS, vol. 24, no. 23, 2022, pp. 4119–23, doi:10.1021/acs.orglett.2c01214.
APA
Ryckaert, B., Hullaert, J., Van Hecke, K., & Winne, J. (2022). Dearomative (3+2) cycloadditions of unprotected indoles. ORGANIC LETTERS, 24(23), 4119–4123. https://doi.org/10.1021/acs.orglett.2c01214
Chicago author-date
Ryckaert, Bram, Jan Hullaert, Kristof Van Hecke, and Johan Winne. 2022. “Dearomative (3+2) Cycloadditions of Unprotected Indoles.” ORGANIC LETTERS 24 (23): 4119–23. https://doi.org/10.1021/acs.orglett.2c01214.
Chicago author-date (all authors)
Ryckaert, Bram, Jan Hullaert, Kristof Van Hecke, and Johan Winne. 2022. “Dearomative (3+2) Cycloadditions of Unprotected Indoles.” ORGANIC LETTERS 24 (23): 4119–4123. doi:10.1021/acs.orglett.2c01214.
Vancouver
1.
Ryckaert B, Hullaert J, Van Hecke K, Winne J. Dearomative (3+2) cycloadditions of unprotected indoles. ORGANIC LETTERS. 2022;24(23):4119–23.
IEEE
[1]
B. Ryckaert, J. Hullaert, K. Van Hecke, and J. Winne, “Dearomative (3+2) cycloadditions of unprotected indoles,” ORGANIC LETTERS, vol. 24, no. 23, pp. 4119–4123, 2022.
@article{8764910,
  abstract     = {{The (3 + 2) cycloaddition of various indoles with a dithioallyl cation affords dearomatized cyclopentannulated adducts, with complete control of regioselectivity and excellent chemo- and diastereoselectivity. The success of the reaction critically relies on the use of an excess of very strong Bronsted acid, which paradoxically prevents carbocationic side reactions. The reaction tolerates sensitive functionalities such as basic amines or free hydroxyls, and we demonstrate its use in late stage derivatization of highly functionalized, unprotected indoles.}},
  author       = {{Ryckaert, Bram and Hullaert, Jan and Van Hecke, Kristof and Winne, Johan}},
  issn         = {{1523-7060}},
  journal      = {{ORGANIC LETTERS}},
  keywords     = {{ALLYL CATIONS,CYCLOPENTANOID,CYCLOADDITION}},
  language     = {{eng}},
  number       = {{23}},
  pages        = {{4119--4123}},
  title        = {{Dearomative (3+2) cycloadditions of unprotected indoles}},
  url          = {{http://doi.org/10.1021/acs.orglett.2c01214}},
  volume       = {{24}},
  year         = {{2022}},
}

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