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Diastereoselective cycloalkylation of phosphoryl and thiophosphoryl acetonitriles by α,ψ-dihalogenalkanes under phase transfer catalysis conditions

Corresponding Author

I. L. Odinets

[email protected]

A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilov str. 28, Moscow B-334, GSP-1, 119991, Russia

A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilov str. 28, Moscow B-334, GSP-1, 119991, RussiaSearch for more papers by this author

N. M. Vinogradova,

N. M. Vinogradova

A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilov str. 28, Moscow B-334, GSP-1, 119991, Russia

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K. A. Lyssenko,

K. A. Lyssenko

A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilov str. 28, Moscow B-334, GSP-1, 119991, Russia

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P. V. Petrovskii,

P. V. Petrovskii

A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilov str. 28, Moscow B-334, GSP-1, 119991, Russia

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T. A. Mastryukova,

T. A. Mastryukova

A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilov str. 28, Moscow B-334, GSP-1, 119991, Russia

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G-V. Röschenthaler,

G-V. Röschenthaler

Institut für Anorganische & Physikalische Chemie, Universität Bremen, Leobener Strasse, 28359 Bremen, Germany

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I. L. Odinets,

Corresponding Author

I. L. Odinets

[email protected]

A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilov str. 28, Moscow B-334, GSP-1, 119991, Russia

A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilov str. 28, Moscow B-334, GSP-1, 119991, RussiaSearch for more papers by this author

N. M. Vinogradova,

N. M. Vinogradova

A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilov str. 28, Moscow B-334, GSP-1, 119991, Russia

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K. A. Lyssenko,

K. A. Lyssenko

A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilov str. 28, Moscow B-334, GSP-1, 119991, Russia

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P. V. Petrovskii,

P. V. Petrovskii

A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilov str. 28, Moscow B-334, GSP-1, 119991, Russia

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T. A. Mastryukova,

T. A. Mastryukova

A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilov str. 28, Moscow B-334, GSP-1, 119991, Russia

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G-V. Röschenthaler,

G-V. Röschenthaler

Institut für Anorganische & Physikalische Chemie, Universität Bremen, Leobener Strasse, 28359 Bremen, Germany

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First published: 30 January 2006

https://doi.org/10.1002/hc.20186

Citations: 14

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Abstract

Cycloalkylation of phosphoryl and thiophosphoryl acetonitriles 2 by α,ψ-dihalogenalkanes was found to proceed diastereoselectively under phase transfer catalytic conditions yielding 1-(phosphoryl)-2-methyl-cycloalkane carbonitriles as trans-isomers with identical configuration of asymmetric cyclic carbon atoms (R_C^* R_C^*). In the case of additional asymmetric phosphorus atom in the starting substrate, trans-isomers are formed as a mixture of diastereomers differing in the configuration of the phosphorus atom (S_P^* R_C^* R_C^* and R_P^* R_C^* R_C^*). © 2006 Wiley Periodicals, Inc. Heteroatom Chem 17:13–21, 2006; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20186

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Diastereoselective cycloalkylation of phosphoryl and thiophosphoryl acetonitriles by α,ψ-dihalogenalkanes under phase transfer catalysis conditions

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Diastereoselective cycloalkylation of phosphoryl and thiophosphoryl acetonitriles by α,ψ-dihalogenalkanes under phase transfer catalysis conditions

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