Catalytic Enantioselective Synthesis of 2,6-Disubstituted Dihydropyrones by Hetero-Diels-Alder Reaction Using Chiral BINOL-Ti(IV) Complex

Yaozong  Huang; Xiaoming  Feng; Bin  Wang; Guolin  Zhang; Yaozhong  Jiang

doi:10.1055/s-2002-35607

LETTER

Catalytic Enantioselective Synthesis of 2,6-Disubstituted Dihydropyrones by Hetero-Diels-Alder Reaction Using Chiral BINOL-Ti(IV) Complex

Yaozong Huang^b, Xiaoming Feng*^a, Bin Wang^b, Guolin Zhang^c, Yaozhong Jiang*^b
^a Sichuan Key Laboratory of Green Chemistry and Technology, The Faculty of Chemistry, Sichuan University, Chengdu 610064, China
Fax: +86(28)85412907; e-Mail: xmfeng@pridns.scu.edu.cn;
^b Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China
^c Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041, China

Abstract

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Abstract

Highly efficient enantioselective synthesis of optically active 2,6-disubstituted dihydropyrones was easily available by hetero-Diels-Alder reaction of aldehydes in presence of 20 mol% (R)-(+)-BINOL-Ti(IV) complex under mild reaction conditions. All reaction products were obtained in moderate to excellent yields (up to 99%) with high enantioselectivities (up to 99% ee).

Key words

hetero-Diels-Alder reaction - dihydropyrones - BINOL

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References

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