Fluoroalkyl N-Triftosylhydrazones as Easily Decomposable Diazo Surrogates for Asymmetric [2+1] Cycloaddition: Synthesis of Chiral Fluoroalkyl Cyclopropenes and Cyclopropanes
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Zhang, Xinyu
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Northeast Normal Univ, Dept Chem, Changchun 130024, Peoples R ChinaNortheast Normal Univ, Dept Chem, Changchun 130024, Peoples R China
Zhang, Xinyu
[1
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Tian, Chunqi
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Northeast Normal Univ, Dept Chem, Changchun 130024, Peoples R ChinaNortheast Normal Univ, Dept Chem, Changchun 130024, Peoples R China
Tian, Chunqi
[1
]
Wang, Zhanjing
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Northeast Normal Univ, Dept Chem, Changchun 130024, Peoples R ChinaNortheast Normal Univ, Dept Chem, Changchun 130024, Peoples R China
Wang, Zhanjing
[1
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Sivaguru, Paramasivam
[1
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Nolan, Steven P.
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Univ Ghent, Dept Chem, B-9000 Ghent, Belgium
Univ Ghent, Ctr Sustainable Chem, B-9000 Ghent, BelgiumNortheast Normal Univ, Dept Chem, Changchun 130024, Peoples R China
Nolan, Steven P.
[2
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Bi, Xihe
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Northeast Normal Univ, Dept Chem, Changchun 130024, Peoples R China
Nankai Univ, State Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R ChinaNortheast Normal Univ, Dept Chem, Changchun 130024, Peoples R China
Bi, Xihe
[1
,4
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机构:
[1] Northeast Normal Univ, Dept Chem, Changchun 130024, Peoples R China
The development of asymmetric carbene transfer reactions using N-sulfonylhydrazones as the diazo surrogate is a long-term issue in organic synthesis since N-sulfonylhydrazones commonly require high temperatures for their decomposition to release reactive diazo compounds. We report on the use of fluoroalkyl-aryl ketone N-triftosylhydrazones as a class of N-sulfonylhydrazone capable of decomposing below 0 degrees C (to -40 degrees C). Their application in asymmetric [2 + 1] cycloadditions with alkynes and alkenes catalyzed by a chiral rhodium catalyst is described. This protocol affords a wide variety of fluoroalkylated cyclopropenes and cyclopropanes in high yields and high enantioselectivity and demonstrates broad functional group tolerance. It is noteworthy that these small-ring products feature a fluoroalkyl chiral quaternary carbon center. The origin of enantioselectivity for the cyclopropenation reaction of N-triftosylhydrazones with alkynes was rationalized by density functional theory calculations.
机构:
Northeast Normal Univ, Dept Chem, Changchun 130024, Peoples R ChinaNortheast Normal Univ, Dept Chem, Changchun 130024, Peoples R China
Zhang, Xinyu
Ning, Yongquan
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Northeast Normal Univ, Dept Chem, Changchun 130024, Peoples R ChinaNortheast Normal Univ, Dept Chem, Changchun 130024, Peoples R China
Ning, Yongquan
Tian, Chunqi
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Northeast Normal Univ, Dept Chem, Changchun 130024, Peoples R ChinaNortheast Normal Univ, Dept Chem, Changchun 130024, Peoples R China
Tian, Chunqi
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Zanoni, Giuseppe
Bi, Xihe
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Northeast Normal Univ, Dept Chem, Changchun 130024, Peoples R China
Nankai Univ, State Key Lab Elemento Organ Chem, Tianjin 300071, Peoples R ChinaNortheast Normal Univ, Dept Chem, Changchun 130024, Peoples R China
机构:
Northeast Normal Univ, Jilin Prov Key Lab Organ Funct Mol Design & Synth, Changchun 130024, Peoples R ChinaNortheast Normal Univ, Jilin Prov Key Lab Organ Funct Mol Design & Synth, Changchun 130024, Peoples R China
Liu, Zhaohong
Li, Qiangqiang
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Northeast Normal Univ, Jilin Prov Key Lab Organ Funct Mol Design & Synth, Changchun 130024, Peoples R ChinaNortheast Normal Univ, Jilin Prov Key Lab Organ Funct Mol Design & Synth, Changchun 130024, Peoples R China
Li, Qiangqiang
Liao, Peiqiu
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Northeast Normal Univ, Jilin Prov Key Lab Organ Funct Mol Design & Synth, Changchun 130024, Peoples R ChinaNortheast Normal Univ, Jilin Prov Key Lab Organ Funct Mol Design & Synth, Changchun 130024, Peoples R China
Liao, Peiqiu
Bi, Xihe
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Northeast Normal Univ, Jilin Prov Key Lab Organ Funct Mol Design & Synth, Changchun 130024, Peoples R China
Nankai Univ, State Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R ChinaNortheast Normal Univ, Jilin Prov Key Lab Organ Funct Mol Design & Synth, Changchun 130024, Peoples R China