Abstract
The effect of diol blocking groups, cyclohexane-1,2-diacetal verses butane-1,2-diacetal, on the asymmetric epoxidation of trans- and cis-alkenes by arabinose-derived ketones is reported. The ketone catalysts with a cyclohexane-1,2-acetal display similar asymmetric induction as those catalysts with a butane-1,2-diacetal in most cases. For (E)-1-benzyloxy-4-hexene, the ee of the enantioselective epoxidation has reached 61% with the cyclohexane-1,2-dineopentyl acetal ketone catalyst.
| Original language | English |
|---|---|
| Pages (from-to) | 883-886 |
| Number of pages | 4 |
| Journal | Tetrahedron Asymmetry |
| Volume | 20 |
| Issue number | 6-8 |
| DOIs | |
| Publication status | Published - 2009 May 7 |
| Externally published | Yes |
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ASJC Scopus subject areas
- Catalysis
- Physical and Theoretical Chemistry
- Organic Chemistry
- Inorganic Chemistry
Cite this
Catalytic asymmetric epoxidation of alkenes with arabinose-derived ketones containing a cyclohexane-1,2-diacetal. / Shing, Tony Kung Ming; Luk, To.
In: Tetrahedron Asymmetry, Vol. 20, No. 6-8, 07.05.2009, p. 883-886.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Catalytic asymmetric epoxidation of alkenes with arabinose-derived ketones containing a cyclohexane-1,2-diacetal
AU - Shing, Tony Kung Ming
AU - Luk, To
PY - 2009/5/7
Y1 - 2009/5/7
N2 - The effect of diol blocking groups, cyclohexane-1,2-diacetal verses butane-1,2-diacetal, on the asymmetric epoxidation of trans- and cis-alkenes by arabinose-derived ketones is reported. The ketone catalysts with a cyclohexane-1,2-acetal display similar asymmetric induction as those catalysts with a butane-1,2-diacetal in most cases. For (E)-1-benzyloxy-4-hexene, the ee of the enantioselective epoxidation has reached 61% with the cyclohexane-1,2-dineopentyl acetal ketone catalyst.
AB - The effect of diol blocking groups, cyclohexane-1,2-diacetal verses butane-1,2-diacetal, on the asymmetric epoxidation of trans- and cis-alkenes by arabinose-derived ketones is reported. The ketone catalysts with a cyclohexane-1,2-acetal display similar asymmetric induction as those catalysts with a butane-1,2-diacetal in most cases. For (E)-1-benzyloxy-4-hexene, the ee of the enantioselective epoxidation has reached 61% with the cyclohexane-1,2-dineopentyl acetal ketone catalyst.
UR - http://www.scopus.com/inward/record.url?scp=65549102446&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=65549102446&partnerID=8YFLogxK
U2 - 10.1016/j.tetasy.2009.02.039
DO - 10.1016/j.tetasy.2009.02.039
M3 - Article
AN - SCOPUS:65549102446
VL - 20
SP - 883
EP - 886
JO - Tetrahedron Asymmetry
JF - Tetrahedron Asymmetry
SN - 0957-4166
IS - 6-8
ER -