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분자활성 촉매반응 연구단
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Disrotatory Ring-Opening of Furans Gives Stereocontrol

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Title
Disrotatory Ring-Opening of Furans Gives Stereocontrol
Author(s)
Jinhoon Jeong; Hyunjoong Kim; Chinmoy K. Hazra; Sukbok Chang; Mu-Hyun Baik
Publication Date
2019-09
Journal
JOURNAL OF ORGANIC CHEMISTRY, v.84, no.17, pp.11061 - 11067
Publisher
AMER CHEMICAL SOC
Abstract
The ring-opening of 2-methylfuran and 2,3-dihydro-5-methylfuran catalyzed by the Lewis acid catalyst tris(pentafluorophenyl)borane in the presence of hydrosilanes was studied using quantum chemical methods. In a previous study, it was suggested that the stereoselective formation of the product is due to a nucleophilic vinylic substitution (SNV) during the reaction. Our calculations show that the pathway involving the SNV reaction is energetically not accessible. Instead, the intramolecular C-O bond cleavage is found to be much more favorable in energy for the ring opening reaction. The experimentally observed excellent stereoselectivity toward the Z-isomer product originates from an intrinsic preference of the furan ring to couple the C-O bond cleavage with a disrotatory motion of the oxygen and carbon fragments. This stereoselective feature is naturally programmed into the furan ring manifold and should be generally exploitable for engineering stereoselective ring-opening processes of bioderived furans. © 2019 American Chemical Society
URI
https://pr.ibs.re.kr/handle/8788114/6438
ISSN
0022-3263
Appears in Collections:
Center for Catalytic Hydrocarbon Functionalizations(분자활성 촉매반응 연구단) > Journal Papers (저널논문)
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