A DFT exploration of the enantioselective rearrangement of cyclohexene oxide to cyclohexenol

Peter Brandt; Per-Ola Norrby; Pher G. Andersson

A DFT exploration of the enantioselective rearrangement of cyclohexene oxide to cyclohexenol

Peter Brandt, Per-Ola Norrby, Pher G. Andersson

Department of Chemistry

Research output: Contribution to journal › Journal article › Research › peer-review

Abstract

In this paper, we present computational results for the (1S,3R,4R)-3-(pyrrolidinyl)-methyl-2-azabicyclo[2.2.1]heptane mediated rearrangement of cyclohexene oxide. The results nicely explain the differences in enantioselectivities between catalytic and stoichiometric mode between different ligands, and provides a rational for the identification of non-stereospecific background reactions as the major cause of decreased enantioselectivity in catalytic reactions for sterically hindered diamines.

Original language	English
Journal	Tetrahedron
Volume	59
Issue number	49
Pages (from-to)	9695-9700
ISSN	0040-4020
Publication status	Published - 2003

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http://dx.doi.org/10.1016/j.tet.2003.10.013

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title = "A DFT exploration of the enantioselective rearrangement of cyclohexene oxide to cyclohexenol",

abstract = "In this paper, we present computational results for the (1S,3R,4R)-3-(pyrrolidinyl)-methyl-2-azabicyclo[2.2.1]heptane mediated rearrangement of cyclohexene oxide. The results nicely explain the differences in enantioselectivities between catalytic and stoichiometric mode between different ligands, and provides a rational for the identification of non-stereospecific background reactions as the major cause of decreased enantioselectivity in catalytic reactions for sterically hindered diamines.",

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T1 - A DFT exploration of the enantioselective rearrangement of cyclohexene oxide to cyclohexenol

AU - Brandt, Peter

AU - Norrby, Per-Ola

AU - Andersson, Pher G.

PY - 2003

Y1 - 2003

N2 - In this paper, we present computational results for the (1S,3R,4R)-3-(pyrrolidinyl)-methyl-2-azabicyclo[2.2.1]heptane mediated rearrangement of cyclohexene oxide. The results nicely explain the differences in enantioselectivities between catalytic and stoichiometric mode between different ligands, and provides a rational for the identification of non-stereospecific background reactions as the major cause of decreased enantioselectivity in catalytic reactions for sterically hindered diamines.

AB - In this paper, we present computational results for the (1S,3R,4R)-3-(pyrrolidinyl)-methyl-2-azabicyclo[2.2.1]heptane mediated rearrangement of cyclohexene oxide. The results nicely explain the differences in enantioselectivities between catalytic and stoichiometric mode between different ligands, and provides a rational for the identification of non-stereospecific background reactions as the major cause of decreased enantioselectivity in catalytic reactions for sterically hindered diamines.

M3 - Journal article

SN - 0040-4020

VL - 59

SP - 9695

EP - 9700

JO - Tetrahedron

JF - Tetrahedron

IS - 49

ER -

A DFT exploration of the enantioselective rearrangement of cyclohexene oxide to cyclohexenol

Abstract

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