Asymmetric synthesis of functionalized pyrrolizidines by an organocatalytic and pot-economy strategy

Chia-Hsin Lin; Bor-Cherng Hong; Gene-Hsiang Lee

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Asymmetric synthesis of functionalized pyrrolizidines by an organocatalytic and pot-economy strategy

机译：有机催化和经济策略对官能化吡咯烷的不对称合成

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An efficient method has been developed for the enantioselective synthesis of tetrahydro-1 H -pyrrolizin-3(2 H )-ones starting from α,β-unsaturated aldehydes via a sequence of asymmetric Michael–oxidative esterification–Michal–reduction–reductive amination–lactamization reactions with high enantioselectivities (93–97% ee). The six-step reaction sequence can be conducted with the pot-economy synthetic strategy with only a one-step purification. The structure and absolute stereochemistry of the intermediates and products were confirmed by X-ray analyses of appropriate products.

机译：已经开发了一种有效的方法，用于通过α，β-不饱和醛从α，β-不饱和醛通过一系列不对称的迈克尔 - 氧化酯化 - 级化 - 还原胺定位进行映射合成致注色合成的方法用高对映射（93-97％EE）的阴囊化反应。六步反应序列可以用盆景合成策略进行，只有一步纯化。通过适当产品的X射线分析证实了中间体和产物的结构和绝对立体化学。

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《RSC Advances》 |2016年第10期|共5页
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Chia-Hsin Lin; Bor-Cherng Hong; Gene-Hsiang Lee;
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1. Asymmetric synthesis of functionalized pyrrolizidines by an organocatalytic and poteconomy strategy [J] . Lin Chia-Hsin, Hong Bor-Cherng, Lee Gene-Hsiang RSC Advances . 2016,第10期

机译：有机催化和双子组织策略对官能化吡咯烷的不对称合成
2. Organocatalytic asymmetric synthesis of highly functionalized pyrrolizidines via cascade Michael/hemi-aminalization reactions of isoindolinones [J] . Scorzelli Francesco, Di Mola Antonia, Croce Gianluca, Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry . 2015,第21期

机译：异吲哚啉酮的级联迈克尔/半氨化反应的有机催化不对称合成高度官能化的吡咯烷
3. One-pot organocatalytic enantioselective Michael addition and aza-cyclization/dehydration cascade reaction strategy: asymmetric synthesis of highly functionalized 1,4-dihydroquinolines [J] . Kim Hanna, Kim Sung-Gon Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry . 2015,第33期

机译：一锅有机催化对映选择性迈克尔加成和氮杂环化/脱水级联反应策略：高功能化1,4-二氢喹啉的不对称合成
4. Enantioselective Organocatalytic Cascade Reaction for the Asymmetric Synthesis of Poly substituted Furofuranes [C] . Efraim Reyes, Garazi Talavera, Jose L. Vicario European Symposium on Organic Chemistry . 2009

机译：对聚取代呋喃脲的不对称合成的对映选择性有机催化级联反应
5. Part I. Asymmetric organocatalysis: (1) Direct enantioselective organocatalytic hydroxymethylation of aldehydes catalyzed by alpha,alpha-diphenylprolinol trimethylsilyl ether: Application in the formal synthesis of (-)-Rasfonin; (2) Synthesis of a novel bicyclic secondary amine organocatalyst: Application to the direct enantioselective organocatalytic hydroxymethylation of aldehydes. Part II. Asymmetric synthesis of bicyclic analogues of the anti-osteoporotic drug risedronate. [D] . Miller, John Robert. 2010

机译：第一部分，不对称有机催化：（1）α，α-二苯基脯氨醇三甲基甲硅烷基醚催化的醛的直接对映选择性有机催化羟甲基化：在（-）-Rasfonin的正式合成中的应用；（2）新型双环仲胺有机催化剂的合成：应用于醛的直接对映选择性有机催化羟甲基化。第二部分抗骨质疏松药物Risedronate的双环类似物的不对称合成。
6. Asymmetric Synthesis of Functionalized Dihydro- and Tetrahydropyrans via an Organocatalytic Domino Michael–Hemiacetalization Reaction [O] . Gregor Urbanietz, Iuliana Atodiresei, Dieter Enders -1

机译：通过有机催化多米诺·迈克尔·半缩醛反应的不对称合成功能化的二氢吡喃和四氢吡喃
7. Asymmetric Organocatalytic Synthesis of Highly Functionalized Spirocyclohexane Indandiones via a One-Pot Michael/Michael/Aldol Sequence [O] . Blümel, Marcus, Chauhan, Pankaj, Vermeeren, Cornelia, 2015

机译：通过一锅Michael / Michael / Aldol序列的不对称有机催化合成高度官能化的螺环己烷茚满

Asymmetric synthesis of functionalized pyrrolizidines by an organocatalytic and pot-economy strategy

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