Stereoselective mannich-type reaction of chiral aldimines with 2-silyloxybutadienes by using trifluoromethanesulfonic acid

Kaori Ishimaru; Takakazu Kojima

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Stereoselective mannich-type reaction of chiral aldimines with 2-silyloxybutadienes by using trifluoromethanesulfonic acid

机译：三氟甲磺酸手性醛亚胺与2-甲硅烷基氧丁二烯的立体选择性曼尼希型反应

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摘要

Novel stereoselective Mannich-type reaction of chiral aldimines with 2-silyloxybutadienes in the presence of trifluoromethanesulfonic acid has been carried out to give the corresponding products, which are not obtained by general Lewis acid-promoted methods, with 70-92% de in 62-74% yield. No cycloadducts were detected in the crude product by ~1H NMR.

机译：在三氟甲磺酸存在下，进行了手性醛亚胺与2-甲硅烷基氧丁二烯的新型立体选择性曼尼希型反应，得到了相应的产物，该产物不能通过一般的路易斯酸促进方法获得，在62-产率74％。通过〜1 H NMR未在粗产物中检测到环加合物。

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《Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry 》 |2003年第29期| 共4页
作者
Kaori Ishimaru; Takakazu Kojima;
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正文语种 eng
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关键词
stereocontrol; imines; dienes; mannich reactions;

机译：立体控制;亚胺;二烯;曼尼希反应;

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专利

1. Stereoselective mannich-type reaction of chiral aldimines with 2-silyloxybutadienes by using trifluoromethanesulfonic acid [J] . Kaori Ishimaru, Takakazu Kojima Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry . 2003 ,第29期

机译：三氟甲磺酸手性醛亚胺与2-甲硅烷基氧丁二烯的立体选择性曼尼希型反应
2. Stereoselective ZrCl4-Catalyzed Mannich-type Reaction of beta-Keto Esters with Chiral Trifluoromethyl Aldimines [J] . Parise Luca, Pellacani Lucio, Sciubba Fabio, The Journal of Organic Chemistry . 2015 ,第16期

机译：β-酮基酯与手性三氟甲基醛亚胺的立体选择性ZrCl4催化曼尼希型反应
3. Asymmetric Mannich-type reactions with a chiral acetate:effect of Lewis acid on activation of aldimine [J] . Susumu Saito, Keiko Hatanaka, Hisashi Yamamoto Tetrahedron . 2001 ,第5期

机译：手性乙酸酯的不对称曼尼希型反应：路易斯酸对醛亚胺活化的影响
4. Enantioselective Direct Mannich-Type Reactions of 2-Benzylpyridine N-Oxides Catalyzed by Chiral Bis(guanidino)iminophosphorane Organosuperbase [C] . Qiupeng Hu, Azusa Kondoh, Masahiro Terada 日本化学会春季年会講演予稿集 . 2018

机译：由手性双（胍基）催化的2-苄基吡啶N-氧化物的对映选择性直接曼尼希型反应
5. Regio- and stereoselective additions to azomethines: Free radical cyclizations and chiral Bronsted acid catalyzed reactions of imines. [D] . Nugent, Benjamin M. 2006

机译：偶氮甲胺的区域和立体选择性加成：自由基环化和手性布朗斯台德酸催化的亚胺反应。
6. Michael Addition Reactions between Chiral Equivalents of a Nucleophilic Glycine and (S)- or (R)-3-(E)-Enoyl-4-phenyl-13-oxazolidin-2-ones as a General Method for Efficient Preparation of β-Substituted Pyroglutamic Acids. Case of Topographically Controlled Stereoselectivity [O] . Vadim A. Soloshonok*, Chaozhong Cai, Takeshi Yamada, -1

机译：亲核甘氨酸与（S）-或（R）-3-（E）-烯丙基 -4-苯基-13-恶唑烷-2-酮的手性当量之间的迈克尔加成反应作为有效制备的一般方法β-取代的焦谷氨酸地形控制立体选择性的情况
7. Chiral Brønsted Acid Catalyzed Highly Stereoselective Mannich-type reaction of Azlactone with Aldimines [O] . Vanessa P. Gonçalves, Rodrigo M. S. Justo, Giovanni W. Amarante 2013

机译：手性Brønsted酸催化了高度立体选择性汉酮型反应的唑酮与醛胺

Stereoselective mannich-type reaction of chiral aldimines with 2-silyloxybutadienes by using trifluoromethanesulfonic acid

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