Chameleon Reactivity of the Allene Bond of 4-Vinylidene-2-oxazolidinone: Novel Through-Space Conjugative Nucleophilic Addition of Electron-Rich Alkenes and Hetero-Nucleophiles

The CαCβ double bond of allene carbamates 1 serves as an electron acceptor similar to the double bond of conjugated enones by means of a through‐space interaction with the NSO2 bond; the carbamate double bond is thus subject to nucleophilic addition for a wide variety of nucleophiles, which procee...

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Published inChemistry : a European journal Vol. 13; no. 34; pp. 9686 - 9702
Main Authors Kimura, Masanari, Horino, Yoshikazu, Mori, Masahiko, Tamaru, Yoshinao
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 01.01.2007
WILEY‐VCH Verlag
Wiley
Subjects
allenes
Chemistry
Chemistry, Multidisciplinary
Diels-Alder reactions
enols
indoles
Physical Sciences
Science & Technology
sulfonamides
COUPLING-CYCLIZATION REACTION
ACID
NITROGEN-HETEROCYCLES
ENOL ETHERS
EFFICIENT SYNTHESIS
FURAN-DIENE
sulfonamides
RADICAL CATALYZED ISOMERIZATION
3+2 CYCLOADDITION
enols
Diels-Alder reactions
allenes
indoles
STEREOSELECTIVE-SYNTHESIS
DEMAND DIELS-ALDER
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Abstract The CαCβ double bond of allene carbamates 1 serves as an electron acceptor similar to the double bond of conjugated enones by means of a through‐space interaction with the NSO2 bond; the carbamate double bond is thus subject to nucleophilic addition for a wide variety of nucleophiles, which proceeds under mild conditions by heating at 70–100 °C. Depending on the kind of nucleophiles, 1 displays three different reaction modes: 1) Typically enol ethers and allylsilanes promote 1,3‐sulfonyl migration of 1 and undergo the inverse electron demand Diels–Alder reaction with the 1‐aza‐1,3‐butadiene intermediates II thus formed to furnish bicyclic 2‐alkoxy‐5‐sulfonyltetrahydropyridines 2 and 2‐silylmethyl‐5‐sulfonyltetrahydropyridines 3, respectively, with high regio‐ and stereoselectivity and retention of configuration of the double bonds of these electron‐rich alkenes; 2) silanes (RnSiH4−n, n=1–3) and thiols deliver the hydride and the thiolate at the Cβ carbon and promote the 1,3‐sulfonyl migration, followed by protonation of the thus‐formed carbamate anion (Z)‐III to provide, for example, (Z)‐4 a and (Z)‐4 j, respectively; 3) alcohols simply add to the CαCβ double bond and provide (E)‐6. Usually, the reaction with alcohols is accompanied by the second pathway, giving rise to, for example, (Z)‐4 b in addition to (E)‐6 b. Phenol engages in the third pathway and provides (E)‐6 g exclusively. Heteroaromatics, such as furans and benzofurans follow the first pathway, however, in a different regioselectivity from enol ethers and allylsilanes, delivering the oxygen atom at the 3‐position of 5‐sulfonyltetrahydropyridines (2 g and 2 h). Indoles, on the other hand, show a dichotomy, equally enjoying the first and the third pathways and provide mixtures of (E)‐7 and (E)‐8, respectively. Through‐space conjugative attack by neutral C‐, O‐, and S‐nucleophiles upon Cβ (see scheme) causes NSO2 bond cleavage of 1 and sulfonyl group migration from N to Cα to generate 3‐sulfonyl‐1‐aza‐1,3‐butadiene, a reactive 4π‐component intermediate for the inverse electron demand Diels–Alder reaction.
AbstractList The CαCβ double bond of allene carbamates 1 serves as an electron acceptor similar to the double bond of conjugated enones by means of a through‐space interaction with the NSO 2 bond; the carbamate double bond is thus subject to nucleophilic addition for a wide variety of nucleophiles, which proceeds under mild conditions by heating at 70–100 °C. Depending on the kind of nucleophiles, 1 displays three different reaction modes: 1) Typically enol ethers and allylsilanes promote 1,3‐sulfonyl migration of 1 and undergo the inverse electron demand Diels–Alder reaction with the 1‐aza‐1,3‐butadiene intermediates II thus formed to furnish bicyclic 2‐alkoxy‐5‐sulfonyltetrahydropyridines 2 and 2‐silylmethyl‐5‐sulfonyltetrahydropyridines 3 , respectively, with high regio‐ and stereoselectivity and retention of configuration of the double bonds of these electron‐rich alkenes; 2) silanes (R n SiH 4− n , n =1–3) and thiols deliver the hydride and the thiolate at the Cβ carbon and promote the 1,3‐sulfonyl migration, followed by protonation of the thus‐formed carbamate anion ( Z )‐ III to provide, for example, ( Z )‐ 4 a and ( Z )‐ 4 j , respectively; 3) alcohols simply add to the CαCβ double bond and provide ( E )‐ 6 . Usually, the reaction with alcohols is accompanied by the second pathway, giving rise to, for example, ( Z )‐ 4 b in addition to ( E )‐ 6 b . Phenol engages in the third pathway and provides ( E )‐ 6 g exclusively. Heteroaromatics, such as furans and benzofurans follow the first pathway, however, in a different regioselectivity from enol ethers and allylsilanes, delivering the oxygen atom at the 3‐position of 5‐sulfonyltetrahydropyridines ( 2 g and 2 h ). Indoles, on the other hand, show a dichotomy, equally enjoying the first and the third pathways and provide mixtures of ( E )‐ 7 and ( E )‐ 8 , respectively.
The Calpha==Cbeta double bond of allene carbamates 1 serves as an electron acceptor similar to the double bond of conjugated enones by means of a through-space interaction with the N--SO2 bond; the carbamate double bond is thus subject to nucleophilic addition for a wide variety of nucleophiles, which proceeds under mild conditions by heating at 70-100 degrees C. Depending on the kind of nucleophiles, 1 displays three different reaction modes: 1) Typically enol ethers and allylsilanes promote 1,3-sulfonyl migration of 1 and undergo the inverse electron demand Diels-Alder reaction with the 1-aza-1,3-butadiene intermediates II thus formed to furnish bicyclic 2-alkoxy-5-sulfonyltetrahydropyridines 2 and 2-silylmethyl-5-sulfonyltetrahydropyridines 3, respectively, with high regio- and stereoselectivity and retention of configuration of the double bonds of these electron-rich alkenes; 2) silanes (RnSiH4-n, n=1-3) and thiols deliver the hydride and the thiolate at the Cbeta carbon and promote the 1,3-sulfonyl migration, followed by protonation of the thus-formed carbamate anion (Z)-III to provide, for example, (Z)-4 a and (Z)-4 j, respectively; 3) alcohols simply add to the Calpha==Cbeta double bond and provide (E)-6. Usually, the reaction with alcohols is accompanied by the second pathway, giving rise to, for example, (Z)-4 b in addition to (E)-6 b. Phenol engages in the third pathway and provides (E)-6 g exclusively. Heteroaromatics, such as furans and benzofurans follow the first pathway, however, in a different regioselectivity from enol ethers and allylsilanes, delivering the oxygen atom at the 3-position of 5-sulfonyltetrahydropyridines (2 g and 2 h). Indoles, on the other hand, show a dichotomy, equally enjoying the first and the third pathways and provide mixtures of (E)-7 and (E)-8, respectively.The Calpha==Cbeta double bond of allene carbamates 1 serves as an electron acceptor similar to the double bond of conjugated enones by means of a through-space interaction with the N--SO2 bond; the carbamate double bond is thus subject to nucleophilic addition for a wide variety of nucleophiles, which proceeds under mild conditions by heating at 70-100 degrees C. Depending on the kind of nucleophiles, 1 displays three different reaction modes: 1) Typically enol ethers and allylsilanes promote 1,3-sulfonyl migration of 1 and undergo the inverse electron demand Diels-Alder reaction with the 1-aza-1,3-butadiene intermediates II thus formed to furnish bicyclic 2-alkoxy-5-sulfonyltetrahydropyridines 2 and 2-silylmethyl-5-sulfonyltetrahydropyridines 3, respectively, with high regio- and stereoselectivity and retention of configuration of the double bonds of these electron-rich alkenes; 2) silanes (RnSiH4-n, n=1-3) and thiols deliver the hydride and the thiolate at the Cbeta carbon and promote the 1,3-sulfonyl migration, followed by protonation of the thus-formed carbamate anion (Z)-III to provide, for example, (Z)-4 a and (Z)-4 j, respectively; 3) alcohols simply add to the Calpha==Cbeta double bond and provide (E)-6. Usually, the reaction with alcohols is accompanied by the second pathway, giving rise to, for example, (Z)-4 b in addition to (E)-6 b. Phenol engages in the third pathway and provides (E)-6 g exclusively. Heteroaromatics, such as furans and benzofurans follow the first pathway, however, in a different regioselectivity from enol ethers and allylsilanes, delivering the oxygen atom at the 3-position of 5-sulfonyltetrahydropyridines (2 g and 2 h). Indoles, on the other hand, show a dichotomy, equally enjoying the first and the third pathways and provide mixtures of (E)-7 and (E)-8, respectively.
The CαCβ double bond of allene carbamates 1 serves as an electron acceptor similar to the double bond of conjugated enones by means of a through‐space interaction with the NSO2 bond; the carbamate double bond is thus subject to nucleophilic addition for a wide variety of nucleophiles, which proceeds under mild conditions by heating at 70–100 °C. Depending on the kind of nucleophiles, 1 displays three different reaction modes: 1) Typically enol ethers and allylsilanes promote 1,3‐sulfonyl migration of 1 and undergo the inverse electron demand Diels–Alder reaction with the 1‐aza‐1,3‐butadiene intermediates II thus formed to furnish bicyclic 2‐alkoxy‐5‐sulfonyltetrahydropyridines 2 and 2‐silylmethyl‐5‐sulfonyltetrahydropyridines 3, respectively, with high regio‐ and stereoselectivity and retention of configuration of the double bonds of these electron‐rich alkenes; 2) silanes (RnSiH4−n, n=1–3) and thiols deliver the hydride and the thiolate at the Cβ carbon and promote the 1,3‐sulfonyl migration, followed by protonation of the thus‐formed carbamate anion (Z)‐III to provide, for example, (Z)‐4 a and (Z)‐4 j, respectively; 3) alcohols simply add to the CαCβ double bond and provide (E)‐6. Usually, the reaction with alcohols is accompanied by the second pathway, giving rise to, for example, (Z)‐4 b in addition to (E)‐6 b. Phenol engages in the third pathway and provides (E)‐6 g exclusively. Heteroaromatics, such as furans and benzofurans follow the first pathway, however, in a different regioselectivity from enol ethers and allylsilanes, delivering the oxygen atom at the 3‐position of 5‐sulfonyltetrahydropyridines (2 g and 2 h). Indoles, on the other hand, show a dichotomy, equally enjoying the first and the third pathways and provide mixtures of (E)‐7 and (E)‐8, respectively. Through‐space conjugative attack by neutral C‐, O‐, and S‐nucleophiles upon Cβ (see scheme) causes NSO2 bond cleavage of 1 and sulfonyl group migration from N to Cα to generate 3‐sulfonyl‐1‐aza‐1,3‐butadiene, a reactive 4π‐component intermediate for the inverse electron demand Diels–Alder reaction.
The Calpha==Cbeta double bond of allene carbamates 1 serves as an electron acceptor similar to the double bond of conjugated enones by means of a through-space interaction with the N--SO2 bond; the carbamate double bond is thus subject to nucleophilic addition for a wide variety of nucleophiles, which proceeds under mild conditions by heating at 70-100 degrees C. Depending on the kind of nucleophiles, 1 displays three different reaction modes: 1) Typically enol ethers and allylsilanes promote 1,3-sulfonyl migration of 1 and undergo the inverse electron demand Diels-Alder reaction with the 1-aza-1,3-butadiene intermediates II thus formed to furnish bicyclic 2-alkoxy-5-sulfonyltetrahydropyridines 2 and 2-silylmethyl-5-sulfonyltetrahydropyridines 3, respectively, with high regio- and stereoselectivity and retention of configuration of the double bonds of these electron-rich alkenes; 2) silanes (RnSiH4-n, n=1-3) and thiols deliver the hydride and the thiolate at the Cbeta carbon and promote the 1,3-sulfonyl migration, followed by protonation of the thus-formed carbamate anion (Z)-III to provide, for example, (Z)-4 a and (Z)-4 j, respectively; 3) alcohols simply add to the Calpha==Cbeta double bond and provide (E)-6. Usually, the reaction with alcohols is accompanied by the second pathway, giving rise to, for example, (Z)-4 b in addition to (E)-6 b. Phenol engages in the third pathway and provides (E)-6 g exclusively. Heteroaromatics, such as furans and benzofurans follow the first pathway, however, in a different regioselectivity from enol ethers and allylsilanes, delivering the oxygen atom at the 3-position of 5-sulfonyltetrahydropyridines (2 g and 2 h). Indoles, on the other hand, show a dichotomy, equally enjoying the first and the third pathways and provide mixtures of (E)-7 and (E)-8, respectively.
The C alpha=C beta double bond of allene carbamates 1 serves as an electron acceptor similar to the double bond of conjugated enones by means of a through-space interaction with the N-SO2 bond: the carbarnate double bond is thus subject to nucleophilic addition for a wide variety of nucleophiles, which proceeds under mild conditions by heating at 70-100 degrees C. Depending on the kind of nucleophiles, 1 displays three different reaction modes: 1) Typically enol ethers and allylsilanes promote 1,3-sulfonyl migration of 1 and undergo the inverse electron demand Diels-Alder reaction with the 1-aza-1,3-butadiene intermediates Pi thus formed to furnish bidyclic 2-alkoxy-5-sulfonyltetrahydropyridines 2 and 2-silylmethyl-5-suffonyltetrahydropyridines 3, respectively, with high regio- and stereoselectivity and retention of configuration of the double bonds of these electron-rich alkenes; 2) silanes (RnSiH4-n, n=1-3) and thiols deliver the hydride and the thiolate at the C beta carbon and promote the 1,3-sulfonyl migration, followed by protonation of the thus-formed carbarnate anion (Z)-III to provide, for example, (Z)-4a and (Z)4j, respectively; 3) alcohols simply add to the C alpha-C beta double bond and provide (E)-6. Usually, the reaction with alcohols is accompanied by the second pathway, giving rise to, for example, (Z)-4b in addition to (E)-6b. Phenol engages in the third pathway and provides (E)-6g exclusively. Heteroaromatics, such as furans and benzofurans follow the first pathway, however, in a different regioselectivity from enol ethers and allylsilanes, delivering the oxygen atom at the 3-position of 5-sulfonyltetrahydropyridines (2g and 2h). Indoles, on the other hand, show a dichotomy, equally enjoying the first and the third pathways and provide mixtures of (E)-7 and (E)-8, respectively.
Author Tamaru, Yoshinao
Horino, Yoshikazu
Mori, Masahiko
Kimura, Masanari
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  givenname: Yoshikazu
  surname: Horino
  fullname: Horino, Yoshikazu
  organization: Department of Applied Chemistry, Graduate School of Science and Engineering, University of Toyama, 3190 Gohuku, Toyama 930-8555, Japan
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  givenname: Masahiko
  surname: Mori
  fullname: Mori, Masahiko
  organization: Graduate School of Science and Technology, Nagasaki University, 1-14 Bunkyo-machi, Nagasaki 852-8521, Japan
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  givenname: Yoshinao
  surname: Tamaru
  fullname: Tamaru, Yoshinao
  email: tamaru@net.nagasaki-u.a
  organization: Department of Applied Chemistry, Faculty of Engineering, Nagasaki University, 1-14 Bunkyo-Machi, Nagasaki 852-8521, Japan
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Issue 34
Keywords COUPLING-CYCLIZATION REACTION
ACID
NITROGEN-HETEROCYCLES
ENOL ETHERS
EFFICIENT SYNTHESIS
FURAN-DIENE
sulfonamides
RADICAL CATALYZED ISOMERIZATION
3+2 CYCLOADDITION
enols
Diels-Alder reactions
allenes
indoles
STEREOSELECTIVE-SYNTHESIS
DEMAND DIELS-ALDER
Language English
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Notes Scientific Research on Priority Areas "Advanced Molecular Transformations of Carbon Resources"
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Ministry of Education, Science, Sports and Culture, Japanese Government, Grant-in-Aid for Scientific Research B
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SSID ssj0009633
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Snippet The CαCβ double bond of allene carbamates 1 serves as an electron acceptor similar to the double bond of conjugated enones by means of a through‐space...
The CαCβ double bond of allene carbamates 1 serves as an electron acceptor similar to the double bond of conjugated enones by means of a through‐space...
The C alpha=C beta double bond of allene carbamates 1 serves as an electron acceptor similar to the double bond of conjugated enones by means of a...
The Calpha==Cbeta double bond of allene carbamates 1 serves as an electron acceptor similar to the double bond of conjugated enones by means of a through-space...
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SubjectTerms allenes
Chemistry
Chemistry, Multidisciplinary
Diels-Alder reactions
enols
indoles
Physical Sciences
Science & Technology
sulfonamides
Title Chameleon Reactivity of the Allene Bond of 4-Vinylidene-2-oxazolidinone: Novel Through-Space Conjugative Nucleophilic Addition of Electron-Rich Alkenes and Hetero-Nucleophiles
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Volume 13
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