Organocatalysis of asymmetric epoxidation by iminium salts using sodium hypochlorite as the stoichiometric oxidant

Philip C. Bulman Page; Phillip Parker; Benjamin R. Buckley; Gerasimos A. Rassias; Donald Bethell

doi:10.1016/j.tet.2009.02.007

Organocatalysis of asymmetric epoxidation by iminium salts using sodium hypochlorite as the stoichiometric oxidant

Philip C. Bulman Page, Phillip Parker, Benjamin R. Buckley, Gerasimos A. Rassias, Donald Bethell

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

30 Citations (Scopus)

Abstract

Iminium salts can provide high selectivity and high efficiency when used as organocatalysts for asymmetric epoxidation. For this purpose, they are normally used in conjunction with Oxone as the stoichiometric oxidant. Oxone, however, has limited stability, is insoluble in most organic solvents, is atom-inefficient, and produces considerable inorganic residue as the by-product of oxidation. In this paper we report for the first time the development of a reaction system driven by sodium hypochlorite as the stoichiometric oxidant.

Original language	English
Pages (from-to)	2910-2915
Number of pages	6
Journal	Tetrahedron
Volume	65
Issue number	15
DOIs	https://doi.org/10.1016/j.tet.2009.02.007
Publication status	Published - 11 Feb 2009

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10.1016/j.tet.2009.02.007

Cite this

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title = "Organocatalysis of asymmetric epoxidation by iminium salts using sodium hypochlorite as the stoichiometric oxidant",

abstract = "Iminium salts can provide high selectivity and high efficiency when used as organocatalysts for asymmetric epoxidation. For this purpose, they are normally used in conjunction with Oxone as the stoichiometric oxidant. Oxone, however, has limited stability, is insoluble in most organic solvents, is atom-inefficient, and produces considerable inorganic residue as the by-product of oxidation. In this paper we report for the first time the development of a reaction system driven by sodium hypochlorite as the stoichiometric oxidant.",

author = "{Bulman Page}, {Philip C.} and Phillip Parker and Buckley, {Benjamin R.} and Rassias, {Gerasimos A.} and Donald Bethell",

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AU - Bulman Page, Philip C.

AU - Parker, Phillip

AU - Buckley, Benjamin R.

AU - Rassias, Gerasimos A.

AU - Bethell, Donald

PY - 2009/2/11

Y1 - 2009/2/11

N2 - Iminium salts can provide high selectivity and high efficiency when used as organocatalysts for asymmetric epoxidation. For this purpose, they are normally used in conjunction with Oxone as the stoichiometric oxidant. Oxone, however, has limited stability, is insoluble in most organic solvents, is atom-inefficient, and produces considerable inorganic residue as the by-product of oxidation. In this paper we report for the first time the development of a reaction system driven by sodium hypochlorite as the stoichiometric oxidant.

AB - Iminium salts can provide high selectivity and high efficiency when used as organocatalysts for asymmetric epoxidation. For this purpose, they are normally used in conjunction with Oxone as the stoichiometric oxidant. Oxone, however, has limited stability, is insoluble in most organic solvents, is atom-inefficient, and produces considerable inorganic residue as the by-product of oxidation. In this paper we report for the first time the development of a reaction system driven by sodium hypochlorite as the stoichiometric oxidant.

U2 - 10.1016/j.tet.2009.02.007

DO - 10.1016/j.tet.2009.02.007

M3 - Article

VL - 65

SP - 2910

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JO - Tetrahedron

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