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.
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收藏
页码：5758 / 5761
页数：4
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