Kinetic and thermodynamic control in the stereoselective formation of trans- and cis-2-ferrocenyl-3-pivaloyl-4-alkyl-1,3-oxazolidin-5-ones

Francisco Alonso; Stephen G. Davies; Almut S. Elend; Andrew D. Smith

doi:10.1039/b814450h

Kinetic and thermodynamic control in the stereoselective formation of trans- and cis-2-ferrocenyl-3-pivaloyl-4-alkyl-1,3-oxazolidin-5-ones

Francisco Alonso, Stephen G. Davies, Almut S. Elend, Andrew D. Smith

Research output: Contribution to journal › Article › peer-review

Abstract

A range of ferrocenylimines derived from ferrocenecarboxaldehyde and the a-amino acids (S)-alanine, (S)-2-aminobutyric acid, (S)-norvaline, (R)-2-phenylglycine, (S)-phenylalanine, O-benzyl (S)-serine, and (S)-tryptophan can be cyclised stereoselectively to afford either the corresponding cis- or trans-2-ferrocenyl-3-pivaloyl-4-alkyl-1,3-oxazolidin-5-ones. The cyclisation reaction shows marked temperature dependence, giving rise preferentially to the trans-oxazolidinone under kinetic control (-78 degrees C) and the thermodynamic cis-oxazolidinone at -15 degrees C to rt.

Original language	English
Pages (from-to)	518-526
Number of pages	9
Journal	Organic & Biomolecular Chemistry
Volume	7
Issue number	3
DOIs	https://doi.org/10.1039/b814450h
Publication status	Published - 2009

Keywords

ALPHA-AMINO-ACIDS
SELF-REGENERATION
ENANTIOSPECIFIC SYNTHESIS
ENANTIOMERICALLY PURE
DERIVATIVES
TRYPTOPHAN
ALDEHYDES
ALANINE
REPRODUCTION
N,O-ACETALS

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10.1039/b814450h

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title = "Kinetic and thermodynamic control in the stereoselective formation of trans- and cis-2-ferrocenyl-3-pivaloyl-4-alkyl-1,3-oxazolidin-5-ones",

abstract = "A range of ferrocenylimines derived from ferrocenecarboxaldehyde and the a-amino acids (S)-alanine, (S)-2-aminobutyric acid, (S)-norvaline, (R)-2-phenylglycine, (S)-phenylalanine, O-benzyl (S)-serine, and (S)-tryptophan can be cyclised stereoselectively to afford either the corresponding cis- or trans-2-ferrocenyl-3-pivaloyl-4-alkyl-1,3-oxazolidin-5-ones. The cyclisation reaction shows marked temperature dependence, giving rise preferentially to the trans-oxazolidinone under kinetic control (-78 degrees C) and the thermodynamic cis-oxazolidinone at -15 degrees C to rt.",

keywords = "ALPHA-AMINO-ACIDS, SELF-REGENERATION, ENANTIOSPECIFIC SYNTHESIS, ENANTIOMERICALLY PURE, DERIVATIVES, TRYPTOPHAN, ALDEHYDES, ALANINE, REPRODUCTION, N,O-ACETALS",

author = "Francisco Alonso and Davies, \{Stephen G.\} and Elend, \{Almut S.\} and Smith, \{Andrew D.\}",

year = "2009",

doi = "10.1039/b814450h",

language = "English",

volume = "7",

pages = "518--526",

journal = "Organic \& Biomolecular Chemistry",

issn = "1477-0539",

publisher = "Royal Society of Chemistry",

number = "3",

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TY - JOUR

T1 - Kinetic and thermodynamic control in the stereoselective formation of trans- and cis-2-ferrocenyl-3-pivaloyl-4-alkyl-1,3-oxazolidin-5-ones

AU - Alonso, Francisco

AU - Davies, Stephen G.

AU - Elend, Almut S.

AU - Smith, Andrew D.

PY - 2009

Y1 - 2009

N2 - A range of ferrocenylimines derived from ferrocenecarboxaldehyde and the a-amino acids (S)-alanine, (S)-2-aminobutyric acid, (S)-norvaline, (R)-2-phenylglycine, (S)-phenylalanine, O-benzyl (S)-serine, and (S)-tryptophan can be cyclised stereoselectively to afford either the corresponding cis- or trans-2-ferrocenyl-3-pivaloyl-4-alkyl-1,3-oxazolidin-5-ones. The cyclisation reaction shows marked temperature dependence, giving rise preferentially to the trans-oxazolidinone under kinetic control (-78 degrees C) and the thermodynamic cis-oxazolidinone at -15 degrees C to rt.

AB - A range of ferrocenylimines derived from ferrocenecarboxaldehyde and the a-amino acids (S)-alanine, (S)-2-aminobutyric acid, (S)-norvaline, (R)-2-phenylglycine, (S)-phenylalanine, O-benzyl (S)-serine, and (S)-tryptophan can be cyclised stereoselectively to afford either the corresponding cis- or trans-2-ferrocenyl-3-pivaloyl-4-alkyl-1,3-oxazolidin-5-ones. The cyclisation reaction shows marked temperature dependence, giving rise preferentially to the trans-oxazolidinone under kinetic control (-78 degrees C) and the thermodynamic cis-oxazolidinone at -15 degrees C to rt.

KW - ALPHA-AMINO-ACIDS

KW - SELF-REGENERATION

KW - ENANTIOSPECIFIC SYNTHESIS

KW - ENANTIOMERICALLY PURE

KW - DERIVATIVES

KW - TRYPTOPHAN

KW - ALDEHYDES

KW - ALANINE

KW - REPRODUCTION

KW - N,O-ACETALS

UR - https://www.scopus.com/pages/publications/58849166835

U2 - 10.1039/b814450h

DO - 10.1039/b814450h

M3 - Article

SN - 1477-0539

VL - 7

SP - 518

EP - 526

JO - Organic & Biomolecular Chemistry

JF - Organic & Biomolecular Chemistry

IS - 3

ER -

Kinetic and thermodynamic control in the stereoselective formation of trans- and cis-2-ferrocenyl-3-pivaloyl-4-alkyl-1,3-oxazolidin-5-ones

Abstract

Keywords

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