Enantioselective Protonation of a Lithium Enolate Derived from 2-Methyl-1-tetralone Using Chiral Sulfonamides

Gregory S.Coumbarides; Jason Eames; J.Erik W.Scheuermann; Kevin F.Sibbons; Michael J.Suggate; Michael Watkinson

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Enantioselective Protonation of a Lithium Enolate Derived from 2-Methyl-1-tetralone Using Chiral Sulfonamides

机译：使用手性磺酰胺衍生自2-甲基-1-丁酮的乙醇酸锂的对映选择性质子化

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The synthesis of enantiomerically enriched (R)-2-methyl-l-tetralone (1) with 77% e.e.was achieved through pro-tonation of its lithium enolate (3) using a C2-syrnmetric tris-sulfonamide (6) as an internal chiral proton source.Access to the complementary (S)-enantiomer 1 with 33% e.e.was achieved using a related C2-symmetric bis-sulfonamide (9) as the chiral proton source.

机译：对映体富集的（R）-2-甲基-1-四氢萘酮（1）的合成是通过使用C2-对称的三磺酰胺（6）作为内质子化其烯酸锂（3）的质子化而实现的使用相关的C2对称双磺酰胺（9）作为手性质子源，可获得具有33％ee的互补（S）-对映体1。

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《Bulletin of the Chemical Society of Japan》 |2005年第5期|共4页
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Gregory S.Coumbarides; Jason Eames; J.Erik W.Scheuermann; Kevin F.Sibbons; Michael J.Suggate; Michael Watkinson;
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1. Enantioselective Protonation of a Lithium Enolate Derived from 2-Methyl-1-tetralone Using Chiral Sulfonamides [J] . Gregory S.Coumbarides, Jason Eames, J.Erik W.Scheuermann, Bulletin of the Chemical Society of Japan . 2005,第5期

机译：使用手性磺酰胺衍生自2-甲基-1-丁酮的乙醇酸锂的对映选择性质子化
2. Chiral Sulfonamide Induced Enantioselective Protonation of Samrium Enolate in the Reaction of α,β-Unsaturated Ester with Ketone [J] . Wei Wang, Ming-Hua Xu, Xin-Sheng Lei, Organic letters . 2000,第24期

机译：α，β-不饱和酯与酮反应中手性磺酰胺诱导的壬酸Sam对映体选择性质子化
3. Enantioselective Protonation of Lithium Enolates with Chiral Imides Possessing a Chiral Amide [J] . Akira Yanagisawa, Tetsuo Kikuchi, Tsuyoshi Watanabe, Bulletin of the Chemical Society of Japan . 1999,第10期

机译：带有手性酰胺的手性酰亚胺的烯醇化锂的对映选择性质子化
4. Direct Enolate Formation of Active Methylene Compounds Using Chiral Palladium Complexes:Catalytic Enantioselective Michael Reaction and Fluorination [C] . Yoshitaka Hamashima, Daido Hotta, Hisashi Takano, Symposium on Organometallic Chemistry . 2003

机译：使用手性钯配合物直接烯醇形成活性亚甲基化合物：催化对映选择性迈克尔反应和氟化
5. Catalytic, enantioselective bifunctional [4+2]-inverse electron demand hetero-Diels-Alder reactions of chiral ketene enolates and o-Benzoquinone derivatives. [D] . Abraham, Ciby Joseph. 2009

机译：手性烯酮烯酸酯和邻苯醌衍生物的催化对映选择性双官能[4 + 2]逆电子需求异Diels-Alder反应。
6. Lithium Enolates in the Enantioselective Construction of Tetrasubstituted Carbon Centers with Chiral Lithium Amides as Non-Covalent Stereodirecting Auxiliaries [O] . Ping Lu, Jeffrey Jackson, Kai Yu, -1

机译：手性锂酰胺作为非共价立体定向助剂的四取代碳中心对映选择性构筑中的烯醇锂
7. Enantioselective Protonation of Enolates: Novel Chiral Proton Sources and Remarkable Effects of the Counter Cation (SYNTHETIC ORGANIC CHEMISTRY - Fine Organic Synthesis) [O] . Fuji Kaoru, Kawabata Takeo, Kuroda Akio, 1996

机译：烯醇盐的对映选择性质子化：新型手性质子来源和抗衡阳离子的显着效果（合成有机化学-精细有机合成）

Enantioselective Protonation of a Lithium Enolate Derived from 2-Methyl-1-tetralone Using Chiral Sulfonamides

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