A Designer Axially Chiral Amino Sulfonamide as an Efficient Organocatalyst for Direct Asymmetric anti-Selective Mannich Reactions and syn-Selective Cross-Aldol Reactions

Kano T; Yamaguchi Y; Maruoka K

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A Designer Axially Chiral Amino Sulfonamide as an Efficient Organocatalyst for Direct Asymmetric anti-Selective Mannich Reactions and syn-Selective Cross-Aldol Reactions

机译：设计师设计的轴向手性氨基磺酰胺可作为有效的有机催化剂，用于直接不对称的反选择性曼尼希反应和同选择性的交叉羟醛反应

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A direct asymmetric Mannich reaction using a novel axially chiral amino sulfonamide (S)-3 that is highly anti- and enantioselective has been developed. For instance, in the presence of a catalytic amount of (S)-3, the reactions between aldehydes and cc-imino esters proceeded smoothly to give anti Mannich products with a significantly higher antilsyn ratio and enantioselectivity than previously possible. By utilizing N-Boc-protected aromatic imines instead of alpha-imino esters, the synthetically useful Boc protecting group and various aromatic or heteroaromatic substituents were installed into the anti Mannich products and consequently the substrate scope of the anti-selective Mannich reaction and the synthetic utility of the anti Mannich products have been expanded. The axially chiral amino sulfonamide (S)-3 has also been successfully applied to asymmetric direct cross-aldol reaction between two different aldehydes. The catalyst (S)-3 has the advantage of giving mainly syn products, whereas proline shows the opposite anti selectivity.

机译：已经开发出使用新型的具有高度抗和对映选择性的轴向手性氨基磺酰胺（S）-3的直接不对称曼尼希反应。例如，在催化量的（S）-3的存在下，醛与α-亚氨基酯之间的反应平稳进行，从而得到具有比以前可能的抗lsyn比和对映选择性明显更高的抗曼尼希产物。通过使用N-Boc保护的芳族亚胺代替α-亚氨基酯，将合成有用的Boc保护基和各种芳族或杂芳族取代基安装到抗曼尼希产品中，因此，抗选择性曼尼希反应和合成的底物范围抗曼尼希产品的用途得到了扩展。轴向手性氨基磺酰胺（S）-3也已成功应用于两种不同醛之间的不对称直接交叉羟醛反应。催化剂（S）-3具有主要产生合成产物的优点，而脯氨酸显示出相反的抗选择性。

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《Chemistry: A European journal》 |2009年第27期|共10页
作者
Kano T; Yamaguchi Y; Maruoka K;
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正文语种 eng
中图分类应用化学;
关键词
aldol reaction; sulfonamides; asymmetric synthesis; Mannich reaction; organocatalysis;

机译：醛醇缩合反应;磺酰胺;不对称合成;曼尼希反应;有机催化;

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1. A Designer Axially Chiral Amino Sulfonamide as an Efficient Organocatalyst for Direct Asymmetric anti-Selective Mannich Reactions and syn-Selective Cross-Aldol Reactions [J] . Kano T, Yamaguchi Y, Maruoka K Chemistry: A European journal . 2009,第27期

机译：设计师设计的轴向手性氨基磺酰胺可作为有效的有机催化剂，用于直接不对称的反选择性曼尼希反应和同选择性的交叉羟醛反应
2. syn-Selective asymmetric cross-aldol reactions between aldehydes and glyoxylic acid derivatives catalyzed by an axially chiral amino sulfonamide [J] . Taichi Kano, Akira Noishiki, Ryu Sakamoto, Chemical Communications . 2011,第38期

机译：轴向手性氨基磺酰胺催化醛与乙醛酸衍生物之间的顺选择性不对称交叉羟醛反应
3. syn-Selective and Enantioselective Direct Cross-Aldol Reactions between Aldehydes Catalyzed by an Axially Chiral Amino Sulfonamide [J] . Taichi Kano, Yukako Yamaguchi, Youhei Tanaka Angewandte Chemie . 2007,第10期

机译：轴向手性氨基磺酰胺催化醛之间的同选择性和对映选择性直接交叉羟醛反应
4. anti-Selective Direct Catalytic Asymmetric Mannich-type Reaction of Hydroxyketone to Provide anti-beta-Amino Alcohols [C] . Naoya Kumagai, Shinji Harada, Shigeki Matsunaga, Symposium on Organometallic Chemistry . 2003

机译：羟基酮的抗选择性直接催化不对称曼尼希型反应提供抗β-氨基醇
5. A. Studies towards the formation of asymmetric quaternary centres via radical allylation. B. Applications of chiral hydrazide organocatalysts to Diels-Alder, hydride reduction, and alpha-chlorination reactions. C. Studies directed towards the synthesis of potential HIV-1 reverse transcriptase inhibitors: 9-Alkylaryl TIBO derivatives. [D] . Aumand, Livia M. 2005

机译：A.关于通过自由基烯丙基化形成不对称四元中心的研究。 B.手性酰肼有机催化剂在Diels-Alder，氢化物还原和α-氯化反应中的应用。 C.针对潜在的HIV-1逆转录酶抑制剂的合成的研究：9-烷基芳基TIBO衍生物。
6. Asymmetric Catalysis Special Feature Part I: Chiral phosphoramide-catalyzed enantioselective directed cross-aldol reactions of aldehydes [O] . Scott E. Denmark, Tommy Bui 2004

机译：不对称催化的特殊功能（第一部分）：手性磷酰胺催化的对映选择性定向醛的交叉羟醛反应
7. Chiral Primary Amine Organocatalysts for Syn-selective Asymmetric Cross-Aldol Reactions [O] . Qiang GAO, Yan LIU, Shengmei LU, 2011

机译：手性伯胺有机催化剂用于同步选择性的不对称交叉醛醇反应

A Designer Axially Chiral Amino Sulfonamide as an Efficient Organocatalyst for Direct Asymmetric anti-Selective Mannich Reactions and syn-Selective Cross-Aldol Reactions

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