Organocatalytic Asymmetric Sequential 1,6-Addition/Acetalization of 1-Oxotetralin-2-carbaldehyde to ortho-Hydroxyphenyl-Substituted para-Quinone Methides for Synthesis of Spiro-3,4-dihydrocoumarins

被引：66
|
作者：
Zhang, Zhi-Pei [1 ]
Chen, Li [1 ]
Li, Xin [1 ]
Cheng, Jin-Pei [1 ]
机构：
[1] Nankai Univ, State Key Lab Elementoorgan Chem, Coll Chem, Collaborat Innovat Ctr Chem Sci & Engn, Tianjin 300071, Peoples R China
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 83卷 / 05期
关键词：
CATALYTIC 1,6-CONJUGATE ADDITION/AROMATIZATION; BETA-ALKYNYL KETONES; ENANTIOSELECTIVE SYNTHESIS; QUATERNARY STEREOCENTER; SULFONIUM SALTS; ONE-POT; DIHYDROCOUMARINS; ACID; STRATEGY; SPIROCYCLOPROPANATION;
D O I：
10.1021/acs.joc.7b03177
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A chiral squaramide catalyzed approach constructing spiro-3,4-dihydrocoumarin motif by the enantioselective 1,6-addition/acetalization reactions of 1-oxotetralin-2-carbaldehydes and ortho-hydroxyphenyl-substituted para-quinone methides followed by an oxidation was developed. The reactions proceeded smoothly with a wide range of p-QMs and 1-oxotetralin-2-carbaldehydes to generate corresponding products in high yields with excellent diastereoselectivities (>19:1 dr) and enantioselectivities (up to 99% ee).
引用
收藏
页码：2714 / 2724
页数：11
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