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Synlett 2002(12): 2122-2124
DOI: 10.1055/s-2002-35607
LETTER
© Georg Thieme Verlag Stuttgart · New York

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

Yaozong Huangb, Xiaoming Feng*a, Bin Wangb, Guolin Zhangc, 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
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Publication History

Received 27 September 2002
Publication Date:
20 November 2002 (online)

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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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5

Compound 2 and 4 were also synthesized by us and applied to the hetero-Diels-Alder reaction of aldehydes promoted by BINOLs-Ti complexes. It was found that (R)-H8-BINOL-Ti(IV) catalytic system could give better enantioselectivity and diastereoselectivity than (R)-BINOL-Ti(IV) complex.