Catalytic asymmetric epoxidation of alkenes with arabinose-derived ketones containing a cyclohexane-1,2-diacetal

Tony K.M. Shing; To Luk

doi:10.1016/j.tetasy.2009.02.039

Catalytic asymmetric epoxidation of alkenes with arabinose-derived ketones containing a cyclohexane-1,2-diacetal

Tony K.M. Shing, To Luk

Department of Chemistry

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

13 Citations (Scopus)

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	https://doi.org/10.1016/j.tetasy.2009.02.039
Publication status	Published - 2009 May 7

ASJC Scopus subject areas

Catalysis
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

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title = "Catalytic asymmetric epoxidation of alkenes with arabinose-derived ketones containing a cyclohexane-1,2-diacetal",

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.",

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AU - Luk, To

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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.

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