Kinetic Resolution of Secondary Alcohols Using Proline-Derived Bicyclic Iminium Salts

Robert Alan Aitken; K Ali; ST Mesher

Kinetic Resolution of Secondary Alcohols Using Proline-Derived Bicyclic Iminium Salts

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Abstract

The proline-derived bicyclic iminium salt 3 can be used to bring about kinetic resolution in its reaction with salts of secondary alcohols to give the corresponding methyl sulfides. Reaction proceeds most efficiently with sodium 1-phenylethoxide in toluene at RT where either 3 or the benzyl salt 14 give e.e.s of 21-25% and changing the heteroatoms present in the sails, the metal cation used and the solvent and temperature all give similar or lower selectivity. (C) 1997 Elsevier Science Ltd.

Original language	English
Pages (from-to)	4179-4182
Number of pages	4
Journal	Tetrahedron Letters
Volume	38
Issue number	23
Publication status	Published - 9 Jun 1997

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title = "Kinetic Resolution of Secondary Alcohols Using Proline-Derived Bicyclic Iminium Salts",

abstract = "The proline-derived bicyclic iminium salt 3 can be used to bring about kinetic resolution in its reaction with salts of secondary alcohols to give the corresponding methyl sulfides. Reaction proceeds most efficiently with sodium 1-phenylethoxide in toluene at RT where either 3 or the benzyl salt 14 give e.e.s of 21-25\% and changing the heteroatoms present in the sails, the metal cation used and the solvent and temperature all give similar or lower selectivity. (C) 1997 Elsevier Science Ltd.",

author = "Aitken, \{Robert Alan\} and K Ali and ST Mesher",

year = "1997",

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language = "English",

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pages = "4179--4182",

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T1 - Kinetic Resolution of Secondary Alcohols Using Proline-Derived Bicyclic Iminium Salts

AU - Aitken, Robert Alan

AU - Ali, K

AU - Mesher, ST

PY - 1997/6/9

Y1 - 1997/6/9

N2 - The proline-derived bicyclic iminium salt 3 can be used to bring about kinetic resolution in its reaction with salts of secondary alcohols to give the corresponding methyl sulfides. Reaction proceeds most efficiently with sodium 1-phenylethoxide in toluene at RT where either 3 or the benzyl salt 14 give e.e.s of 21-25% and changing the heteroatoms present in the sails, the metal cation used and the solvent and temperature all give similar or lower selectivity. (C) 1997 Elsevier Science Ltd.

AB - The proline-derived bicyclic iminium salt 3 can be used to bring about kinetic resolution in its reaction with salts of secondary alcohols to give the corresponding methyl sulfides. Reaction proceeds most efficiently with sodium 1-phenylethoxide in toluene at RT where either 3 or the benzyl salt 14 give e.e.s of 21-25% and changing the heteroatoms present in the sails, the metal cation used and the solvent and temperature all give similar or lower selectivity. (C) 1997 Elsevier Science Ltd.

UR - https://www.scopus.com/pages/publications/0030920893

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M3 - Article

SN - 0040-4039

VL - 38

SP - 4179

EP - 4182

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 23

ER -

Kinetic Resolution of Secondary Alcohols Using Proline-Derived Bicyclic Iminium Salts

Abstract

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