Enantioselective olefin epoxidation using homologous amine and iminium catalysts—a direct comparison

Maria-Héléna Goncalves; Alexandre Martinez; Stéphane Grass; Philip C. Bulman Page; Jérôme Lacour

doi:10.1016/j.tetlet.2006.05.132

Enantioselective olefin epoxidation using homologous amine and iminium catalysts—a direct comparison

Maria-Héléna Goncalves, Alexandre Martinez, Stéphane Grass, Philip C. Bulman Page, Jérôme Lacour

Chemistry of Materials and Catalysis

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

37 Citations (Scopus)

Abstract

Homologous biphenyl and (diastereomeric) binaphthyl tertiary azepines and quaternary iminium salts were prepared from (+)-(S,S)-L-acetonamine. Both the amines and iminium ions behave as effective catalysts for the enantioselective epoxidation of unfunctionalized olefins (ee up to 83%).

Original language	English
Pages (from-to)	5297-5301
Number of pages	5
Journal	Tetrahedron Letters
Volume	47
Issue number	30
Early online date	12 Jun 2006
DOIs	https://doi.org/10.1016/j.tetlet.2006.05.132
Publication status	Published - 24 Jul 2006

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10.1016/j.tetlet.2006.05.132

Cite this

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title = "Enantioselective olefin epoxidation using homologous amine and iminium catalysts—a direct comparison",

abstract = "Homologous biphenyl and (diastereomeric) binaphthyl tertiary azepines and quaternary iminium salts were prepared from (+)-(S,S)-L-acetonamine. Both the amines and iminium ions behave as effective catalysts for the enantioselective epoxidation of unfunctionalized olefins (ee up to 83%).",

author = "Maria-H{\'e}l{\'e}na Goncalves and Alexandre Martinez and St{\'e}phane Grass and {Bulman Page}, {Philip C.} and J{\'e}r{\^o}me Lacour",

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T1 - Enantioselective olefin epoxidation using homologous amine and iminium catalysts—a direct comparison

AU - Goncalves, Maria-Héléna

AU - Martinez, Alexandre

AU - Grass, Stéphane

AU - Bulman Page, Philip C.

AU - Lacour, Jérôme

PY - 2006/7/24

Y1 - 2006/7/24

N2 - Homologous biphenyl and (diastereomeric) binaphthyl tertiary azepines and quaternary iminium salts were prepared from (+)-(S,S)-L-acetonamine. Both the amines and iminium ions behave as effective catalysts for the enantioselective epoxidation of unfunctionalized olefins (ee up to 83%).

AB - Homologous biphenyl and (diastereomeric) binaphthyl tertiary azepines and quaternary iminium salts were prepared from (+)-(S,S)-L-acetonamine. Both the amines and iminium ions behave as effective catalysts for the enantioselective epoxidation of unfunctionalized olefins (ee up to 83%).

U2 - 10.1016/j.tetlet.2006.05.132

DO - 10.1016/j.tetlet.2006.05.132

M3 - Article

VL - 47

SP - 5297

EP - 5301

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 30

ER -