Synlett 2007(14): 2147-2157  
DOI: 10.1055/s-2007-984917
ACCOUNT
© Georg Thieme Verlag Stuttgart · New York

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;
Further Information

Publication History

Received 27 January 2007
Publication Date:
20 July 2007 (online)

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