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

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

Fingerprint

ASJC Scopus subject areas

Catalysis
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

Cite this

Shing, T. K. M., & Luk, T. (2009). Catalytic asymmetric epoxidation of alkenes with arabinose-derived ketones containing a cyclohexane-1,2-diacetal. Tetrahedron Asymmetry, 20(6-8), 883-886. https://doi.org/10.1016/j.tetasy.2009.02.039

@article{d184b645f2864267872bda00dfe36be5,

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.",

author = "Shing, {Tony K.M.} and To Luk",

year = "2009",

month = may

day = "7",

doi = "10.1016/j.tetasy.2009.02.039",

language = "English",

volume = "20",

pages = "883--886",

journal = "Tetrahedron Asymmetry",

issn = "0957-4166",

publisher = "Elsevier Limited",

number = "6-8",

}

TY - JOUR

T1 - Catalytic asymmetric epoxidation of alkenes with arabinose-derived ketones containing a cyclohexane-1,2-diacetal

AU - Shing, Tony K.M.

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 -

Access to Document

10.1016/j.tetasy.2009.02.039