Asymmetric Intramolecular Amination Catalyzed with CpIr-SPDO via Nitrene Transfer for Synthesis of Spiro-Quaternary Indolinone

An asymmetric intramolecular spiro-amination to high steric hindering α-C–H bond of 1,3-dicarbonyl via nitrene transfer using inactive aryl azides has been carried out by developing a novel Cp*Ir­(III)-SPDO (spiro-pyrrolidine oxazoline) catalyst, thereby enabling the first successful construction of...

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Published inJournal of the American Chemical Society Vol. 146; no. 28; pp. 18841 - 18847
Main Authors Wei, Shi-Qiang, Li, Zi-Hao, Wang, Shuang-Hu, Chen, Hua, Wang, Xiao-Yu, Gu, Yun-Zhou, Zhang, Ye, Wang, Hong, Ding, Tong-Mei, Zhang, Shu-Yu, Tu, Yong-Qiang
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 17.07.2024
Amer Chemical Soc
Subjects
amination
azides
catalysts
Chemistry
Chemistry, Multidisciplinary
enols
ligands
Physical Sciences
Science & Technology
CROSS-COUPLING REACTIONS
INSERTION
AZIRIDINATION
ACCESS
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Abstract An asymmetric intramolecular spiro-amination to high steric hindering α-C–H bond of 1,3-dicarbonyl via nitrene transfer using inactive aryl azides has been carried out by developing a novel Cp*Ir­(III)-SPDO (spiro-pyrrolidine oxazoline) catalyst, thereby enabling the first successful construction of structurally rigid spiro-quaternary indolinone cores with moderate to high yields and excellent enantioselectivities. DFT computations support the presence of double bridging H–F bonds between [SbF6]− and both the ligand and substrate, which favors the plane-differentiation of the enol π-bond for nitrenoid attacking. These findings open up numerous opportunities for the development of new asymmetric nitrene transfer systems.
AbstractList An asymmetric intramolecular spiro-amination to high steric hindering α-C–H bond of 1,3-dicarbonyl via nitrene transfer using inactive aryl azides has been carried out by developing a novel Cp*Ir­(III)-SPDO (spiro-pyrrolidine oxazoline) catalyst, thereby enabling the first successful construction of structurally rigid spiro-quaternary indolinone cores with moderate to high yields and excellent enantioselectivities. DFT computations support the presence of double bridging H–F bonds between [SbF₆]⁻ and both the ligand and substrate, which favors the plane-differentiation of the enol π-bond for nitrenoid attacking. These findings open up numerous opportunities for the development of new asymmetric nitrene transfer systems.
An asymmetric intramolecular spiro-amination to high steric hindering -C-H bond of 1,3-dicarbonyl via nitrene transfer using inactive aryl azides has been carried out by developing a novel Cp*Ir(III)-SPDO (spiro-pyrrolidine oxazoline) catalyst, thereby enabling the first successful construction of structurally rigid spiro-quaternary indolinone cores with moderate to high yields and excellent enantioselectivities. DFT computations support the presence of double bridging H-F bonds between [SbF ] and both the ligand and substrate, which favors the plane-differentiation of the enol π-bond for nitrenoid attacking. These findings open up numerous opportunities for the development of new asymmetric nitrene transfer systems.
An asymmetric intramolecular spiro-amination to high steric hindering alpha-C-H bond of 1,3-dicarbonyl via nitrene transfer using inactive aryl azides has been carried out by developing a novel Cp*Ir(III)-SPDO (spiro-pyrrolidine oxazoline) catalyst, thereby enabling the first successful construction of structurally rigid spiro-quaternary indolinone cores with moderate to high yields and excellent enantioselectivities. DFT computations support the presence of double bridging H-F bonds between [SbF6](-) and both the ligand and substrate, which favors the plane-differentiation of the enol pi-bond for nitrenoid attacking. These findings open up numerous opportunities for the development of new asymmetric nitrene transfer systems.
An asymmetric intramolecular spiro-amination to high steric hindering α-C-H bond of 1,3-dicarbonyl via nitrene transfer using inactive aryl azides has been carried out by developing a novel Cp*Ir(III)-SPDO (spiro-pyrrolidine oxazoline) catalyst, thereby enabling the first successful construction of structurally rigid spiro-quaternary indolinone cores with moderate to high yields and excellent enantioselectivities. DFT computations support the presence of double bridging H-F bonds between [SbF6]- and both the ligand and substrate, which favors the plane-differentiation of the enol π-bond for nitrenoid attacking. These findings open up numerous opportunities for the development of new asymmetric nitrene transfer systems.An asymmetric intramolecular spiro-amination to high steric hindering α-C-H bond of 1,3-dicarbonyl via nitrene transfer using inactive aryl azides has been carried out by developing a novel Cp*Ir(III)-SPDO (spiro-pyrrolidine oxazoline) catalyst, thereby enabling the first successful construction of structurally rigid spiro-quaternary indolinone cores with moderate to high yields and excellent enantioselectivities. DFT computations support the presence of double bridging H-F bonds between [SbF6]- and both the ligand and substrate, which favors the plane-differentiation of the enol π-bond for nitrenoid attacking. These findings open up numerous opportunities for the development of new asymmetric nitrene transfer systems.
An asymmetric intramolecular spiro-amination to high steric hindering α-C–H bond of 1,3-dicarbonyl via nitrene transfer using inactive aryl azides has been carried out by developing a novel Cp*Ir­(III)-SPDO (spiro-pyrrolidine oxazoline) catalyst, thereby enabling the first successful construction of structurally rigid spiro-quaternary indolinone cores with moderate to high yields and excellent enantioselectivities. DFT computations support the presence of double bridging H–F bonds between [SbF6]− and both the ligand and substrate, which favors the plane-differentiation of the enol π-bond for nitrenoid attacking. These findings open up numerous opportunities for the development of new asymmetric nitrene transfer systems.
Author Ding, Tong-Mei
Li, Zi-Hao
Gu, Yun-Zhou
Zhang, Ye
Wang, Hong
Tu, Yong-Qiang
Chen, Hua
Wang, Shuang-Hu
Wei, Shi-Qiang
Zhang, Shu-Yu
Wang, Xiao-Yu
AuthorAffiliation College of Pharmaceutical Science and Collaborative Innovation Cent of Yangtze River Delta Region Green Pharmaceuticals
School of Chemistry and Chemical Engineering, Frontier Scientific Center of Transformative Molecules, Shanghai Key Laboratory of Chiral Drugs and Engineering
State Key Laboratory of Applied Organic Chemistry and College of Chemistry and Chemical Engineering
AuthorAffiliation_xml – name: College of Pharmaceutical Science and Collaborative Innovation Cent of Yangtze River Delta Region Green Pharmaceuticals
– name: State Key Laboratory of Applied Organic Chemistry and College of Chemistry and Chemical Engineering
– name: School of Chemistry and Chemical Engineering, Frontier Scientific Center of Transformative Molecules, Shanghai Key Laboratory of Chiral Drugs and Engineering
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SSID ssj0004281
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Snippet An asymmetric intramolecular spiro-amination to high steric hindering α-C–H bond of 1,3-dicarbonyl via nitrene transfer using inactive aryl azides has been...
An asymmetric intramolecular spiro-amination to high steric hindering alpha-C-H bond of 1,3-dicarbonyl via nitrene transfer using inactive aryl azides has been...
An asymmetric intramolecular spiro-amination to high steric hindering -C-H bond of 1,3-dicarbonyl via nitrene transfer using inactive aryl azides has been...
An asymmetric intramolecular spiro-amination to high steric hindering α-C-H bond of 1,3-dicarbonyl via nitrene transfer using inactive aryl azides has been...
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StartPage 18841
SubjectTerms amination
azides
catalysts
Chemistry
Chemistry, Multidisciplinary
enols
ligands
Physical Sciences
Science & Technology
Title Asymmetric Intramolecular Amination Catalyzed with CpIr-SPDO via Nitrene Transfer for Synthesis of Spiro-Quaternary Indolinone
URI http://dx.doi.org/10.1021/jacs.4c05560
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