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 | |
| Publication status | Published - 2004 Jul 26 |
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Keywords
- Asymmetric epoxidation
ASJC Scopus subject areas
- Biochemistry
- Drug Discovery
- Organic Chemistry
Cite this
On the scope of diastereoselective epoxidation of various chiral auxiliaries derived enones : The conformational analysis of camphor derived N- and O-enones. / Lee, Wei Der; Chiu, Ching Chen; Hsu, Hua Lin; Chen, Kwunmin.
In: Tetrahedron, Vol. 60, No. 31, 26.07.2004, p. 6657-6664.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - On the scope of diastereoselective epoxidation of various chiral auxiliaries derived enones
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
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
UR - http://www.scopus.com/inward/record.url?scp=4143141244&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=4143141244&partnerID=8YFLogxK
U2 - 10.1016/j.tet.2004.05.095
DO - 10.1016/j.tet.2004.05.095
M3 - Article
AN - SCOPUS:4143141244
VL - 60
SP - 6657
EP - 6664
JO - Tetrahedron
JF - Tetrahedron
SN - 0040-4020
IS - 31
ER -