Asymmetric Tandem Michael-Aldol Reactions between 3-Cinnamoyloxazolidine-2-thiones and Aldehydes

Hironori Kinoshita; Takashi Osamura; Kazumi Mizuno; Sayaka Kinoshita; Tatsunori Iwamura

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Asymmetric Tandem Michael-Aldol Reactions between 3-Cinnamoyloxazolidine-2-thiones and Aldehydes

机译：3-肉桂酰基恶唑烷-2-硫酮与醛之间的不对称串联迈克尔-阿尔多反应

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Reactions between chiral 3-cinnamoyl-4-methyl-5-phenyl-1,3-oxazoli-dine-2-thiones and aromatic aldehydes in the presence of BF_3Et_2O diastereoselec-tively produced tricyclic compounds incorporating a bridgehead carbon bound to four heteroatoms in high yields.Four stereocenters were induced during the reaction.The tricyclic products were transformed into propane-1,3-diols bearing three consecutive stereocenters by acid hydrolysis,S-methylation,and reductive removal of the chiral auxiliary.

机译：在BF_3Et_2O非对映生成的三环化合物的存在下，手性3-肉桂酰基-4-甲基-5-苯基-1,3-恶唑二胺-2-硫酮与芳族醛之间的反应在反应过程中诱导了四个立体中心。通过酸水解，S-甲基化和还原去除手性助剂，将三环产物转化为带有三个连续立体中心的丙烷-1,3-二醇。

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《Chemistry: A European journal》 |2006年第14期|共9页
作者
Hironori Kinoshita; Takashi Osamura; Kazumi Mizuno; Sayaka Kinoshita; Tatsunori Iwamura;
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正文语种 eng
中图分类化学;
关键词
aldehydes; asymmetric synthesis; oxazolidinethiones; sulfanylpropanediols; tandem Michael-aldol reactions;

机译：醛;不对称合成;恶唑烷硫酮;亚磺酰基丙二醇;级联迈克尔-阿尔道反应;

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1. Asymmetric Tandem Michael-Aldol Reactions between 3-Cinnamoyloxazolidine-2-thiones and Aldehydes [J] . Hironori Kinoshita, Takashi Osamura, Kazumi Mizuno, Chemistry: A European journal . 2006,第14期

机译：3-肉桂酰基恶唑烷-2-硫酮与醛之间的不对称串联迈克尔-阿尔多反应
2. Stereoselective Michael-Aldol Tandem Reaction of Phenylselenomagnesium Bromide with Acetylenic Sulfones and Aldehydes. An Efficient Synthesis of Polyfunctionalized Allylic Alcohols [J] . Xian Huang, Meihua Xie Organic letters . 2002,第8期

机译：苯基硒化溴化镁与乙炔砜和醛类的立体选择性Michael-Aldol串联反应。多官能化烯丙醇的高效合成
3. Asymmetric synthesis of α-alkylidene-β-hydroxy-γ- butyrolactones via enantioselective tandem michael-aldol reaction [J] . Lee S.I., Jang J.H., Hwang G.-S., The Journal of Organic Chemistry . 2013,第2期

机译：通过对映选择性串联迈克尔-阿尔道反应不对称合成α-亚烷基-β-羟基-γ-丁内酯
4. Direct asymmetric Michael reaction of α,β-unsaturated aldehydes and ketones catalyzed by two secondary amine catalysts [C] . Umekubo Nariyoshi, Terunuma Takahiro, Hayashi Yujiro 日本化学会春季年会講演予稿集 . 2018

机译：由两个仲胺催化剂催化的α，β-不饱和醛和酮的直接不对称迈克尔反应
5. Part I. Asymmetric synthesis of bicyclic analogues of risedronate as molecular probes of the mechanism of action of bisphosphonate antiosteoporotic drugs and potentially more efficacious antiosteoporotic agents. Part II. Facile preparation and functionalization of chiral stabilized ylides from common chiral auxiliaries using the Bestmann ylide and their use in Wittig reactions. Part III. Asymmetric organocatalysis: 1. An investigation of alpha-hydroxylation of aldehydes; 2. Synthesis of a novel camphor-based alpha-aminotetrazole organocatalyst. [D] . Song, Xinyi. 2007

机译：第一部分：利塞膦酸盐双环类似物的不对称合成，作为双膦酸盐类抗骨质疏松药和潜在更有效的抗骨质疏松药作用机理的分子探针。第二部分使用Bestmann内酯从常见手性助剂轻松制备和官能化手性稳定化的叶基及其在Wittig反应中的用途。第三部分不对称有机催化：1.醛的α-羟基化研究； 2.合成新的基于樟脑的α-氨基四唑有机催化剂。
6. Gold-catalyzed tandem reactions of amide–aldehyde–alkyne coupling and cyclization-synthesis of 245-trisubstituted oxazoles [O] . Pierre Querard, Simon A. Girard, Nick Uhlig, 2015

机译：金催化的酰胺-醛-炔烃偶联串联反应和245-三取代的恶唑的环化合成
7. Enantioselective Organocatalytic Tandem Michael-Aldol Reactions: One-Pot Synthesis of Chiral Thiochromenes [O] . -1

机译：对映选择性有机催化串联迈克尔 - 醛醇反应：单罐合成手性硫代噻吩

Asymmetric Tandem Michael-Aldol Reactions between 3-Cinnamoyloxazolidine-2-thiones and Aldehydes

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