On the scope of diastereoselective epoxidation of various chiral auxiliaries derived enones: The conformational analysis of camphor derived N- and O-enones

Wei Der Lee; Ching Chen Chiu; Hua Lin Hsu; Kwunmin Chen

doi:10.1016/j.tet.2004.05.095

On the scope of diastereoselective epoxidation of various chiral auxiliaries derived enones: The conformational analysis of camphor derived N- and O-enones

Wei Der Lee, Ching Chen Chiu, Hua Lin Hsu, Kwunmin Chen

Department of Chemistry

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

17 Citations (Scopus)

Abstract

Various camphor derived N- and O-enones were treated with selected oxidants to provide the corresponding epoxides in a wide range of diastereoselectivity. For camphorsultam derived activated alkenes, high to excellent stereoselectivities were obtained when the s-trans enones were treated with methyl(trifluoromethyl)dioxirane. On the other hand, for exo-10,10-diphenyl-2, 10-camphanediol (3) and exo-10,10-diphenyl-10-methoxy-2-camphanol (4) derived alkenes, the use of s-cis enones gave the desired epoxide with excellent diastereoselectivity under the same reaction conditions. The stereoselectivity was highly dependent on the geometry of the auxiliaries derived enones and the stereochemical induction is discussed.

Original language	English
Pages (from-to)	6657-6664
Number of pages	8
Journal	Tetrahedron
Volume	60
Issue number	31
DOIs	https://doi.org/10.1016/j.tet.2004.05.095
Publication status	Published - 2004 Jul 26

Keywords

Asymmetric epoxidation

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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title = "On the scope of diastereoselective epoxidation of various chiral auxiliaries derived enones: The conformational analysis of camphor derived N- and O-enones",

abstract = "Various camphor derived N- and O-enones were treated with selected oxidants to provide the corresponding epoxides in a wide range of diastereoselectivity. For camphorsultam derived activated alkenes, high to excellent stereoselectivities were obtained when the s-trans enones were treated with methyl(trifluoromethyl)dioxirane. On the other hand, for exo-10,10-diphenyl-2, 10-camphanediol (3) and exo-10,10-diphenyl-10-methoxy-2-camphanol (4) derived alkenes, the use of s-cis enones gave the desired epoxide with excellent diastereoselectivity under the same reaction conditions. The stereoselectivity was highly dependent on the geometry of the auxiliaries derived enones and the stereochemical induction is discussed.",

keywords = "Asymmetric epoxidation",

author = "Lee, {Wei Der} and Chiu, {Ching Chen} and Hsu, {Hua Lin} and Kwunmin Chen",

note = "Funding Information: Financial support by the National Science Council of the Republic of China (NSC 92-2113-M-003-017 and NSC 92-2751-B-001-014-Y) and the National Taiwan Normal University (ORD 91-2) are gratefully acknowledged. ",

year = "2004",

month = jul,

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doi = "10.1016/j.tet.2004.05.095",

language = "English",

volume = "60",

pages = "6657--6664",

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T2 - The conformational analysis of camphor derived N- and O-enones

AU - Lee, Wei Der

AU - Chiu, Ching Chen

AU - Hsu, Hua Lin

AU - Chen, Kwunmin

N1 - Funding Information: Financial support by the National Science Council of the Republic of China (NSC 92-2113-M-003-017 and NSC 92-2751-B-001-014-Y) and the National Taiwan Normal University (ORD 91-2) are gratefully acknowledged.

PY - 2004/7/26

Y1 - 2004/7/26

N2 - Various camphor derived N- and O-enones were treated with selected oxidants to provide the corresponding epoxides in a wide range of diastereoselectivity. For camphorsultam derived activated alkenes, high to excellent stereoselectivities were obtained when the s-trans enones were treated with methyl(trifluoromethyl)dioxirane. On the other hand, for exo-10,10-diphenyl-2, 10-camphanediol (3) and exo-10,10-diphenyl-10-methoxy-2-camphanol (4) derived alkenes, the use of s-cis enones gave the desired epoxide with excellent diastereoselectivity under the same reaction conditions. The stereoselectivity was highly dependent on the geometry of the auxiliaries derived enones and the stereochemical induction is discussed.

AB - Various camphor derived N- and O-enones were treated with selected oxidants to provide the corresponding epoxides in a wide range of diastereoselectivity. For camphorsultam derived activated alkenes, high to excellent stereoselectivities were obtained when the s-trans enones were treated with methyl(trifluoromethyl)dioxirane. On the other hand, for exo-10,10-diphenyl-2, 10-camphanediol (3) and exo-10,10-diphenyl-10-methoxy-2-camphanol (4) derived alkenes, the use of s-cis enones gave the desired epoxide with excellent diastereoselectivity under the same reaction conditions. The stereoselectivity was highly dependent on the geometry of the auxiliaries derived enones and the stereochemical induction is discussed.

KW - Asymmetric epoxidation

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