Highly Efficient Asymmetric Synthesis of Vinylic Amino Alcohols by Zn-Promoted Benzoyloxyallylation of Chiral N-tert-Butanesulfinyl Imines: Facileand Rapid Access to (–)-Cytoxazone

Min Liu; Xing-Wen Sun; Ming-Hua Xu; Guo-Qiang Lin

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Highly Efficient Asymmetric Synthesis of Vinylic Amino Alcohols by Zn-Promoted Benzoyloxyallylation of Chiral N-tert-Butanesulfinyl Imines: Facileand Rapid Access to (–)-Cytoxazone

机译：锌通过手性N-叔丁亚磺酰基亚胺的锌促进的苯甲酰氧基化反应，高效地不对称合成乙烯基氨基醇：简便快速进入（-）-Cytoxazone

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An efficient and convenienta-hydroxyallylation approach for theasymmetric synthesis of a variety of (3-amino-a-vinyl alcohols has been suc-cessfully developed. A wide range ofvinylic amino alcohol derivatives couldbe obtained in very good yields andwith excellent diastereomeric ratios ofup to 99:1 in favor of anti isomers byhighly diastereoselective Zn-promoted benzoyloxyallylation of chiral N-tert-butanesulfinyl imines with 3-bromopro-penyl benzoate at room temperature.In particular, excellent enantioinduc-tion of the two new stereogenic centers was observed, with up to 98 % ee. Themethod provides a new route for thedirect a-hydroxyallylation of imines ina highly stereoselective manner. More-over, the synthetic value of the methodhas also been demonstrated by themost concise and straightforward syn-thesis of (—)-cytoxazone yet reported.

机译：已成功开发了一种有效且方便的羟基化方法，用于不对称合成多种（3-氨基-α-乙烯基醇）。可以以很高的收率和高达99的非对映异构体比率获得各种乙烯基氨基醇衍生物1：1的抗异构体是在室温下手性N-叔丁亚磺酰基亚胺与3-溴原戊烯基苯甲酸酯的高度非对映选择性Zn促进的苯甲酰氧基化，特别是在两个新的立体异构中心观察到出色的对映体诱导作用到98％ee。该方法为亚胺以高度立体选择性的方式直接进行α-羟基羟化提供了一条新途径，此外，该方法的合成价值也已通过（-）-cytoxazone的最简明直接的合成得到了证明。报告。

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《Chemistry: A European journal》 |2009年第39期|共8页
作者
Min Liu; Xing-Wen Sun; Ming-Hua Xu; Guo-Qiang Lin;
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正文语种 eng
中图分类应用化学;
关键词
amino alcohols; asym-metric synthesis; chiral auxiliaries; (—)cytoxazone; hydroxyallylation;

机译：氨基醇;不对称合成;手性助剂;（—）cytoxazone;羟基化;

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1. Highly Efficient Asymmetric Synthesis of Vinylic Amino Alcohols by Zn-Promoted Benzoyloxyallylation of Chiral N-tert-Butanesulfinyl Imines: Facileand Rapid Access to (–)-Cytoxazone [J] . Min Liu, Xing-Wen Sun, Ming-Hua Xu, Chemistry: A European journal . 2009,第39期

机译：锌通过手性N-叔丁亚磺酰基亚胺的锌促进的苯甲酰氧基化反应，高效地不对称合成乙烯基氨基醇：简便快速进入（-）-Cytoxazone
2. Regio- and diastereoselective Reformatsky reaction of chiral fluoroalkyl alpha,beta-unsaturated N-tert-butanesulfinyl ketimines: Efficient asymmetric synthesis of beta-fluoroalkyl beta-vinyl beta-amino esters [J] . Peng Ying-Ying, Liu Peng, Liu Zhen-Jiang, Tetrahedron . 2018,第24期

机译：Chiroal氟代烷基α，β-不饱和N-叔丁烷磺酰酮的regio-and DiapereOlecleative Reformatsky Refordatsky反应：β-氟代烷基β-乙烯基β-氨基酯的有效不对称合成
3. Remarkable salt effect on in-mediated allylation of N-tert-butanesulfinyl imines in aqueous media: Highly practical asymmetric synthesis of chiral homoallylic amines and isoindolinones [J] . Sun XW, Liu M, Xu MH, Organic letters . 2008,第6期

机译：盐对水介质中N-叔丁亚磺酰基亚胺介导的烯丙基化的影响：手性均烯丙基胺和异吲哚啉酮的高度实用的不对称合成
4. Synthesis of Chiral N-α-pyridylmethyl Amino Alcohols and Their Application in Catalytic Asymmetric Addition of Diethylzinc to Aromatic Aldehydes [C] . Hongying Yun International symposium for Chinese organic chemists . 2000

机译：手性N-α-吡啶基甲基氨基醇的合成及其在催化不对称加入芳族醛的催化不对称中的应用
5. New methods for the synthesis of α-amino acid derivatives from N-tert-butanesulfinyl imines and the synthesis and application of novel amino acid based N-tert-butanesulfinyl amide organocatalysts [D] . Herbage, Melissa Ann 2009

机译：由N-叔丁亚磺酰基亚胺合成α-氨基酸衍生物的新方法以及基于氨基酸的新型N-叔丁亚磺酰基酰胺有机催化剂的合成与应用
6. Asymmetric Hydrophosphylation of Chiral N-Phosphonyl Imines Provides an Efficient Approach to Chiral α-Amino Phosphonates [O] . Parminder Kaur, Walter Wever, Trideep Rajale, -1

机译：手性正膦酰亚胺的不对称氢磷化提供了一种有效的手性α-氨基膦酸酯方法
7. Remarkable Salt Effect on In-Mediated Allylation of N-tert-Butanesulfinyl Imines in Aqueous Media: Highly Practical Asymmetric Synthesis of Chiral Homoallylic Amines and Isoindolinones [O] . -1

机译：在含水介质中的N-TERT-丁磺酰基亚胺内介导的烯丙基溶液的显着盐效应：高度实际的不对称合成手性主体胺和异吲哚酮
8. Chiral Synthesis via Organoboranes. 18. Selective Reductions. 43. Diisopinocampheylchloroborane as an Excellent Chiral Reducing Reagent for the Synthesis of Halo Alcohols of High Enantiomeric Purity. A Highly Enantioselective Synt [R] . Srebnik, M., Ramachandran, P. V., Brown, H. C. 1988

机译：有机硼烷的手性合成。 18.选择性削减。 43. Diisopinocampheylchloroborane作为一种优良的手性还原剂，用于合成高对映体纯度的卤代醇。高度对映选择性合成

Highly Efficient Asymmetric Synthesis of Vinylic Amino Alcohols by Zn-Promoted Benzoyloxyallylation of Chiral N-tert-Butanesulfinyl Imines: Facileand Rapid Access to (–)-Cytoxazone

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