Enantioselective Synthesis of Spiro Chroman‐Isoindolinones via Formal (4+2) Cycloaddition of In Situ‐Generated ortho ‐Quinone Methides with 3‐Methylene Isoindolinones
Publication type: Journal Article
Publication date: 2022-07-06
scimago Q1
wos Q1
SJR: 0.930
CiteScore: 8.0
Impact factor: 4.0
ISSN: 16154150, 16154169
Catalysis
Organic Chemistry
Abstract
Using chiral phosphoric acids as organocatalysts, a formal asymmetric (4+2) cycloaddition of 3-methylene isoindolinone and in situ-generated ortho-quinone methide substrates is disclosed. This reaction exhibited a broad substrate scope with various substituted cyclic enamides and ortho-hydroxybenzyl alcohol derivatives to construct a series of spiro chroman-isoindolinones containing spiro-N,O-heterocycles with 56 to 93% ee. This strategy demonstrates significant potential towards establishing a chiral spiro-N,O-aminal systems bearing two chiral carbon centers, including a tetrasubstituted carbon stereocenter.
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Wang T., Bo H., Wang Y. Q. Enantioselective Synthesis of Spiro Chroman‐Isoindolinones via Formal (4+2) Cycloaddition of In Situ‐Generated ortho ‐Quinone Methides with 3‐Methylene Isoindolinones // Advanced Synthesis and Catalysis. 2022. Vol. 364. No. 15. pp. 2596-2605.
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Wang T., Bo H., Wang Y. Q. Enantioselective Synthesis of Spiro Chroman‐Isoindolinones via Formal (4+2) Cycloaddition of In Situ‐Generated ortho ‐Quinone Methides with 3‐Methylene Isoindolinones // Advanced Synthesis and Catalysis. 2022. Vol. 364. No. 15. pp. 2596-2605.
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TY - JOUR
DO - 10.1002/adsc.202200350
UR - https://doi.org/10.1002/adsc.202200350
TI - Enantioselective Synthesis of Spiro Chroman‐Isoindolinones via Formal (4+2) Cycloaddition of In Situ‐Generated ortho ‐Quinone Methides with 3‐Methylene Isoindolinones
T2 - Advanced Synthesis and Catalysis
AU - Wang, Tao
AU - Bo, HUANG
AU - Wang, You Qing
PY - 2022
DA - 2022/07/06
PB - Wiley
SP - 2596-2605
IS - 15
VL - 364
SN - 1615-4150
SN - 1615-4169
ER -
Cite this
BibTex (up to 50 authors)
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@article{2022_Wang,
author = {Tao Wang and HUANG Bo and You Qing Wang},
title = {Enantioselective Synthesis of Spiro Chroman‐Isoindolinones via Formal (4+2) Cycloaddition of In Situ‐Generated ortho ‐Quinone Methides with 3‐Methylene Isoindolinones},
journal = {Advanced Synthesis and Catalysis},
year = {2022},
volume = {364},
publisher = {Wiley},
month = {jul},
url = {https://doi.org/10.1002/adsc.202200350},
number = {15},
pages = {2596--2605},
doi = {10.1002/adsc.202200350}
}
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MLA
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Wang, Tao, et al. “Enantioselective Synthesis of Spiro Chroman‐Isoindolinones via Formal (4+2) Cycloaddition of In Situ‐Generated ortho ‐Quinone Methides with 3‐Methylene Isoindolinones.” Advanced Synthesis and Catalysis, vol. 364, no. 15, Jul. 2022, pp. 2596-2605. https://doi.org/10.1002/adsc.202200350.