Hydrosilylation-Promoted Furan Diels–Alder Cycloadditions with Stereoselectivity Controlled by the Silyl Group
Publication type: Journal Article
Publication date: 2019-12-06
scimago Q1
wos Q1
SJR: 5.554
CiteScore: 22.5
Impact factor: 15.6
ISSN: 00027863, 15205126
PubMed ID:
31809027
General Chemistry
Catalysis
Biochemistry
Colloid and Surface Chemistry
Abstract
Herein we describe an unprecedented B(C6F5)3-catalyzed cascade reaction of N-allyl-N-furfurylamides involving an initial intramolecular furan Diels-Alder reaction and subsequent ether cleavage. The reaction has a broad substrate scope, even tolerating a trialkyl-substituted olefin as the dienophile, which has not previously been observed with conventional furan Diels-Alder reactions. In addition, the relative configuration of the product can be controlled by the choice of the silyl group: reactions involving Et3SiH and iPr3SiH gave different diastereomers. Control experiments and the computational studies revealed that the steric bulk of the silyl group plays a key role in determining the reaction pathway and thus the relative configuration of the product.
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Total citations:
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Citations from 2024:
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(17%)
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Liu Z., Zhang M., Wang X. C. Hydrosilylation-Promoted Furan Diels–Alder Cycloadditions with Stereoselectivity Controlled by the Silyl Group // Journal of the American Chemical Society. 2019. Vol. 142. No. 1. pp. 581-588.
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Liu Z., Zhang M., Wang X. C. Hydrosilylation-Promoted Furan Diels–Alder Cycloadditions with Stereoselectivity Controlled by the Silyl Group // Journal of the American Chemical Society. 2019. Vol. 142. No. 1. pp. 581-588.
Cite this
RIS
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TY - JOUR
DO - 10.1021/jacs.9b11909
UR - https://doi.org/10.1021/jacs.9b11909
TI - Hydrosilylation-Promoted Furan Diels–Alder Cycloadditions with Stereoselectivity Controlled by the Silyl Group
T2 - Journal of the American Chemical Society
AU - Liu, Zhi-Yun
AU - Zhang, Ming
AU - Wang, Xiao Chen
PY - 2019
DA - 2019/12/06
PB - American Chemical Society (ACS)
SP - 581-588
IS - 1
VL - 142
PMID - 31809027
SN - 0002-7863
SN - 1520-5126
ER -
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BibTex (up to 50 authors)
Copy
@article{2019_Liu,
author = {Zhi-Yun Liu and Ming Zhang and Xiao Chen Wang},
title = {Hydrosilylation-Promoted Furan Diels–Alder Cycloadditions with Stereoselectivity Controlled by the Silyl Group},
journal = {Journal of the American Chemical Society},
year = {2019},
volume = {142},
publisher = {American Chemical Society (ACS)},
month = {dec},
url = {https://doi.org/10.1021/jacs.9b11909},
number = {1},
pages = {581--588},
doi = {10.1021/jacs.9b11909}
}
Cite this
MLA
Copy
Liu, Zhi-Yun, et al. “Hydrosilylation-Promoted Furan Diels–Alder Cycloadditions with Stereoselectivity Controlled by the Silyl Group.” Journal of the American Chemical Society, vol. 142, no. 1, Dec. 2019, pp. 581-588. https://doi.org/10.1021/jacs.9b11909.
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