Enantioselective Organocatalytic Michael Addition-Cyclization Cascade of Cyclopentane-1,2-dione with Substituted (E)-2-oxobut-3-enoates

被引:7
作者
Preegel, Gert [1 ]
Ilmarinen, Kaja [1 ]
Jaerving, Ivar [1 ]
Kanger, Tonis [1 ]
Pehk, Tonis [2 ]
Lopp, Margus [1 ]
机构
[1] Tallinn Univ Technol, Dept Chem, EE-12618 Tallinn, Estonia
[2] NICPB, EE-12618 Tallinn, Estonia
来源
SYNTHESIS-STUTTGART | 2015年 / 47卷 / 23期
关键词
organocatalysis; cascade reactions; atropisomerism; stereoselectivity; ALPHA-KETO ESTERS; ASYMMETRIC-SYNTHESIS; HENRY REACTION; DERIVATIVES; EFFICIENT; SQUARAMIDE; CATALYST; 4-HYDROXYCOUMARIN; ATROPISOMERISM; KETOESTERS;
D O I
10.1055/s-0035-1560347
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An organocatalytic cascade Michael addition-cyclization reaction of cyclopentane-1,2-dione with substituted (E)-2-oxobut-3-enoates, creating two stereocenters and giving bicyclic hemiacetals 3 in excellent yield (up to 93%) and enantioselectivity (up to 96% ee) was developed. From 2-chlorophenyl-substituted (E)-2-oxobut-3-enoate, the adduct revealed pseudo-atropisomerism from the hindered rotation of the phenyl ring. The hemiacetal 3 was reduced with Et3SiH and Lewis acid affording substituted 1,2-cyclopentanedione 8, and disilylated with an excess of TMSOTf and Et3N to the dienol disilyl ether 9.
引用
收藏
页码:3805 / 3812
页数:8
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