Asymmetric Hetero-Diels-Alder Reactions of Danishefsky's and Brassard's Dienes with Aldehydes

Lili Lin; Xiaohua Liu; Xiaoming Feng

doi:10.1055/s-2007-984917

ACCOUNT

Asymmetric Hetero-Diels-Alder Reactions of Danishefsky's and Brassard's Dienes with Aldehydes

Lili Lin, Xiaohua Liu, Xiaoming Feng*
Sichuan Key Laboratory of Green Chemistry and Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, P. R. of China
Fax: +86(28)85418249; e-Mail: xmfeng@scu.edu.cn;

Abstract

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Abstract

The asymmetric hetero-Diels-Alder reactions of three Danishefsky"s dienes and two Brassard"s dienes with aldehydes that have been performed in our group are presented. (R)-1,1¢-Bi-2-naphthol [(R)-BINOL] and its derivatives complexed with tetraisopropoxytitanium(IV) [Ti(Oi-Pr)₄] were efficient catalytic systems for the reactions with Danishefsky"s dienes, proceeding via a Mukaiyama aldol pathway. Meanwhile, tridentate Schiff base ligands complexed with Ti(Oi-Pr)₄ or copper(II) triflate [Cu(OTf)₂] were efficient for the reactions of Brassard’s dienes, following the Diels-Alder pathway.

1 Introduction

2 Asymmetric Hetero-Diels-Alder Reactions of Danishefsky"s and Danishefsky-Type Dienes

2.1 Asymmetric Hetero-Diels-Alder Reactions of Danishefsky"s Diene

2.2 Asymmetric Hetero-Diels-Alder Reactions of a Danishefsky-Type Diene To Give 2,6-Disubstituted Dihydropyrones

2.3 Asymmetric Hetero-Diels-Alder Reactions of a Danishefsky-Type Diene To Give 2,5-Disubstituted Dihydropyrones

3 Asymmetric Hetero-Diels-Alder Reactions of Brassard"s and Brassard-Type Dienes

3.1 Asymmetric Hetero-Diels-Alder Reactions of Brassard"s Diene

3.2 Asymmetric Hetero-Diels-Alder Reactions of a Brassard-Type Diene

4 Summary and Perspectives

Key words

asymmetric catalysis - Diels-Alder reactions - heterocycles - Lewis acids - Schiff bases

Full Text

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