Synthesis, volume 48, issue 04, pages 512-519
Gold(I)-Catalyzed Stereospecific [4+3]-Cycloaddition Reaction of 1-(Alk-1-ynyl)cyclopropyl Ketones with Nitrones: A Modular Entry to Enantioenriched 5,7-Fused Bicyclic Furo[3,4-d][1,2]oxazepines
Publication type: Journal Article
Publication date: 2016-01-11
Catalysis
Organic Chemistry
Abstract
In our previous study, a gold(I)-catalyzed stereoselective formal [4+3]-cycloaddition reaction of 1-(alk-1-ynyl)cyclopropyl ketones with nitrones was found to afford 5,7-fused bicyclic furo[3,4-d][1,2]oxazepines in good to excellent yields with high diastereoselectivity catalyzed by (triphenylphosphine)gold(I) triflate. In order to gain insight into the mechanism of this [4+3] cycloaddition process, an enantioselective version used a MeO-DTBM-BIPHEP derived gold(I) complex as the catalyst, which resulted in the kinetic resolution of the 1-(alk-1-ynyl)cyclopropyl ketones, affording the recovered ketones in high yield with excellent enantioselectivity. An interesting chirality transfer was observed in the gold(I)-catalyzed [4+3] cycloaddition of optically active 1-(alk-1-ynyl)cyclopropyl ketones with nitrones, indicating the reaction undergoes a stereospecific SN2-type ring-opening of the cyclopropane.
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Xiao Y., Xiao Y., Zhang J. Gold(I)-Catalyzed Stereospecific [4+3]-Cycloaddition Reaction of 1-(Alk-1-ynyl)cyclopropyl Ketones with Nitrones: A Modular Entry to Enantioenriched 5,7-Fused Bicyclic Furo[3,4-d][1,2]oxazepines // Synthesis. 2016. Vol. 48. No. 04. pp. 512-519.
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Xiao Y., Xiao Y., Zhang J. Gold(I)-Catalyzed Stereospecific [4+3]-Cycloaddition Reaction of 1-(Alk-1-ynyl)cyclopropyl Ketones with Nitrones: A Modular Entry to Enantioenriched 5,7-Fused Bicyclic Furo[3,4-d][1,2]oxazepines // Synthesis. 2016. Vol. 48. No. 04. pp. 512-519.
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TY - JOUR
DO - 10.1055/s-0035-1561276
UR - https://doi.org/10.1055/s-0035-1561276
TI - Gold(I)-Catalyzed Stereospecific [4+3]-Cycloaddition Reaction of 1-(Alk-1-ynyl)cyclopropyl Ketones with Nitrones: A Modular Entry to Enantioenriched 5,7-Fused Bicyclic Furo[3,4-d][1,2]oxazepines
T2 - Synthesis
AU - Xiao, Yuanjing
AU - Xiao, Yuanjing
AU - Zhang, Junliang
PY - 2016
DA - 2016/01/11
PB - Georg Thieme Verlag KG
SP - 512-519
IS - 04
VL - 48
SN - 0039-7881
SN - 1437-210X
ER -
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@article{2016_Xiao,
author = {Yuanjing Xiao and Yuanjing Xiao and Junliang Zhang},
title = {Gold(I)-Catalyzed Stereospecific [4+3]-Cycloaddition Reaction of 1-(Alk-1-ynyl)cyclopropyl Ketones with Nitrones: A Modular Entry to Enantioenriched 5,7-Fused Bicyclic Furo[3,4-d][1,2]oxazepines},
journal = {Synthesis},
year = {2016},
volume = {48},
publisher = {Georg Thieme Verlag KG},
month = {jan},
url = {https://doi.org/10.1055/s-0035-1561276},
number = {04},
pages = {512--519},
doi = {10.1055/s-0035-1561276}
}
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Xiao, Yuanjing, et al. “Gold(I)-Catalyzed Stereospecific [4+3]-Cycloaddition Reaction of 1-(Alk-1-ynyl)cyclopropyl Ketones with Nitrones: A Modular Entry to Enantioenriched 5,7-Fused Bicyclic Furo[3,4-d][1,2]oxazepines.” Synthesis, vol. 48, no. 04, Jan. 2016, pp. 512-519. https://doi.org/10.1055/s-0035-1561276.
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