Highly Efficient and General Synthetic Method of Various Retinyl Ethers

Jun Sup Lee; Young Cheol Jeong; Minkoo Ji; Woonphil Baik; Sijoon Lee; Sangho Koo

doi:10.1055/s-2004-830873

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Synlett 2004(11): 1937-1940
DOI: 10.1055/s-2004-830873

LETTER

Highly Efficient and General Synthetic Method of Various Retinyl Ethers

Jun Sup Lee^a, Young Cheol Jeong^a, Minkoo Ji^a, Woonphil Baik^a, Sijoon Lee^b, Sangho Koo*^a
^a Department of Chemistry, Myong Ji University, Yongin, Kyunggi-Do, 449-728, Korea
Fax: +82(31)3357248; e-Mail: sangkoo@mju.ac.kr;
^b Chemical Research Center, SK Corporation, Yusung, Taejon, 305-370, Korea

Further Information

Publication History

Received 12 May 2004
Publication Date:
06 August 2004 (online)

Abstract
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Abstract

Bromination of 4 by PBr₃ under Cu^I catalyst produces the ambidextrous allylic halide 5 regioselectively and stereoselectively. Hetero nucleophiles distinguish the allylic carbon containing Br from the one containing Cl in 5 to give the heteroatom-substituted C₅ allylic chloride 3. The Julia olefination reaction with the C₁₅ sulfone 2 provides diverse retinyl ethers 1.

Key words

retinyl ethers - olefination - stereoselective synthesis - sulfones - vitamins

References

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16

Decomposition of the NMR sample of retinyl acetate in CDCl₃ at ambient temperature was noticed within one week.