Chiral phosphoramide-catalyzed, enantioselective, directed cross-aldol reactions of aldehydes

Denmark SE; Bui T

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Chiral phosphoramide-catalyzed, enantioselective, directed cross-aldol reactions of aldehydes

机译：手性磷酰胺催化的对映体选择性，定向的醛的交叉羟醛反应

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摘要

Catalytic, enantioselective, directed cross-aldol reactions of aldehydes are described. The addition of isobutyraldehyde trichlorosilyl enolate 2 to various aldehydes in the presence of 10 mol % bisphosphoramide 4 provides aldol products in high yields with moderate to good enantioselectivities. The reaction works well with a wide range of aromatic, olefinic, and aliphatic aldehydes. Enantioselectivities are highly dependent on the electronic nature of the aldehyde substituent. Hammett studies reveal that enantioselectivity increases as aldehydes become either more electron rich or more electron poor.

机译：描述了醛的催化，对映选择性，定向的交叉羟醛反应。在10mol％双磷酰胺4的存在下向各种醛中添加异丁醛三氯甲硅烷基烯醇酸酯2提供高产率的醛醇产物，具有中等至良好的对映选择性。该反应可与多种芳族，烯烃和脂族醛很好地配合。对映选择性高度取决于醛取代基的电子性质。 Hammett研究表明，随着醛变得越来越富电子或越来越贫电子，对映选择性增加。

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来源
《Proceedings of the National Academy of Sciences of the United States of America》 |2004年第15期|p.5439-5444|共6页
作者
Denmark SE; Bui T;
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作者单位

Denmark SE, Univ Illinois, Dept Chem, Roger Adams Lab 245, Box 18-5,600 S Mathews Ave, Urbana, IL 61801, USA;

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收录信息美国《科学引文索引》(SCI);美国《生物学医学文摘》(MEDLINE);美国《化学文摘》(CA);
原文格式 PDF
正文语种 eng
中图分类自然科学总论;
关键词
Hammett substituent constants; Lewis base activation; Copper(ii); complexes; Asymmetric reactions; Solid-state; Additions; Acids; Allylation; Chemistry; Ketones;

机译：哈米特取代基常数;路易斯碱活化;铜（ii）;络合物;不对称反应;固态;加成;酸;烯丙基化;化学;酮;

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1. 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
2. Mechanistic Insights into the Chiral Phosphoramide-Catalyzed,Enantioselective Crossed-Aldol Reactions of Aldehydes [J] . Scott E.Denmark, Tommy Bui The Journal of Organic Chemistry . 2005,第25期

机译：机械见解的手性磷酰胺催化，醛的对映选择性交叉-羟醛反应
3. Trichlorosilyl triflate-mediated enantioselective directed cross-aldol reaction between ketones using a chiral phosphine oxide as an organocatalyst [J] . Shohei Aoki, Shunsuke Kotani, Masaharu Sugiura, Chemical Communications . 2012,第44期

机译：使用手性氧化膦作为有机催化剂的三氯甲硅烷基三氟甲磺酸酯介导的酮之间的对映选择性定向丙二醛交叉反应
4. Theoretical study of stereoselectivity for syn-selective cross-aldol reactions of aldehydes catalyzed by chiral diamine organocatalysts [C] . Chengyan Zhao, Aiping Fu, Hongliang Li, 2013 International conference on computational sciences and engineering . 2013

机译：手性二胺有机催化剂催化醛的顺-选择性跨羟醛反应的立体选择性理论研究
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 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 phosphoramide-catalyzed, enantioselective, directed cross-aldol reactions of aldehydes [O] . Denmark, Scott E., Bui, Tommy 2004

机译：手性磷酰胺催化的对映体选择性，定向的醛的交叉羟醛反应
8. Chiral Oxazaborolidines as Catalysts for the Enantioselective Addition of Diethylzinc to Aldehydes [R] . Joshi, N. N., Srebnik, M., Brown, H. C. 1989

机译：手性恶唑硼烷作为二乙基锌对醛的不对称加成催化剂

Chiral phosphoramide-catalyzed, enantioselective, directed cross-aldol reactions of aldehydes

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