Asymmetric Synthesis of 3,4-Dihydrocoumarin Motif with an All-Carbon Quaternary Stereocenter via a Michael-Acetalization Sequence with Bifunctional Amine-thiourea Organocatalysts

被引：59

作者：

Hong, Bor-Cherng ^{[1
]}

Kotame, Prakash ^{[1
]}

Lee, Gene-Hsiang ^{[2
]}

机构：

[1] Natl Chung Cheng Univ, Dept Chem & Biochem, Chiayi 621, Taiwan

[2] Natl Taiwan Univ, Instrumentat Ctr, Taipei 106, Taiwan

来源：

ORGANIC LETTERS | 2011年 / 13卷 / 21期

关键词：

DIELS-ALDER REACTIONS; O-QUINONE METHIDES; ALPHA; BETA-UNSATURATED ALDEHYDES; ENANTIOSELECTIVE SYNTHESIS; ALDOL CONDENSATION; SUBSTITUTED CHROMANS; EFFICIENT SYNTHESIS; ADDITION-REACTIONS; FORMAL SYNTHESIS; C-C;

D O I：

10.1021/ol202331j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Asymmetric domino Michael acetalization reactions of 2-hydroxynitrostyrene and 2-oxocyclohexanecarbaldehyde with a bifunctional thioureatertiary-amine organocatalyst, e.g., the Takemoto catalyst, followed by oxidation providing the 1',3-spiro-2'-oxocyclohexan-3,4-dihydrocoumarin having one all-carbon quaternary stereocenter with excellent diastereo- and enantioselectivities (up to >99% ee), are described. The structures and absolute configurations of the products were confirmed by X-ray analysis.

引用

收藏

页码：5758 / 5761

页数：4

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