3-取代联萘酚钛配合物催化反式-1-甲氧基-2-甲基-3-三甲基硅氧基-1,3-丁二烯与芳香醛和脂肪醛的高度对映选择性杂环狄尔斯-阿尔德反应

Highly enantioselective hetero- Diels-Alder reaction of trans-1-methoxy- 2-methyl-3-trimethylsiloxybuta-1,3-diene with aromatic and aliphatic aldehydes catalyzed by 3-substituted BINOL-titanium complex.

作者信息

Yang Xin-Bin, Feng Jie, Zhang Ji, Wang Na, Wang Li, Liu Jun-Liang, Yu Xiao-Qi

机构信息

Department of Chemistry, Key Laboratory of Green Chemistry and Technology (Ministry of Education), and West China Hospital, West China Medical School, Sichuan University, Chengdu, Sichuan 610041, PR China.

出版信息

Org Lett. 2008 Mar 20;10(6):1299-302. doi: 10.1021/ol8001706. Epub 2008 Feb 28.

DOI:10.1021/ol8001706

PMID:18303907

Abstract

3-diphenylhydroxymethyl-substituted BINOL-titanium complex prepared in situ was found to be a highly efficient catalyst for hetero-Diels-Alder reaction of diene 1 with both aromatic and aliphatic aldehydes to give 2,5-disubstituted dihydropyrone in up to 99% yield and 99% ee.

摘要

原位制备的3-二苯基羟甲基取代的联萘酚钛配合物被发现是一种高效催化剂，可用于二烯1与芳香醛和脂肪醛的杂环狄尔斯-阿尔德反应，以高达99%的产率和99%的对映体过量得到2,5-二取代二氢吡喃酮。