K3PO4-promoted domino reactions: diastereoselective synthesis of trans-2,3-dihydrobenzofurans from salicyl N-tert-butanesulfinyl imines and sulfur ylides

Zhang Minxuan; Lu Tianyu; Zhao Yun; Xie Guixian; Miao Zhiwei

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K3PO4-promoted domino reactions: diastereoselective synthesis of trans-2,3-dihydrobenzofurans from salicyl N-tert-butanesulfinyl imines and sulfur ylides

机译：K3PO4-促进的多米诺反应：从水杨基N-叔丁沙磺酰亚胺和硫酰胺中的反式选择性合成反式-2,3-二氢苯并呋喃

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An efficient domino annulation between sulfur ylides and salicyl N-tert-butylsulfinyl imines was developed. The reaction proceeds with a diastereodivergent process, the configuration of the sulfinyl group determining the stereochemical course of the reaction. The method allows the synthesis of a highly substituted trans-2,3-dihydrobenzofuran skeleton with high yield and good chemo- and diastereoselectivity.

机译：硫酰胺与水杨基N-叔丁基磺酰亚胺之间的有效多米诺环素被开发出来。反应进行了一种不适化的方法，磺基的构氨基确定反应的立体化学过程。该方法允许合成高度取代的反式-2,3-二氢脲骨浆，其具有高产率和良好的化学和非对映选择性。

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《RSC Advances》 |2019年第21期|共8页
作者
Zhang Minxuan; Lu Tianyu; Zhao Yun; Xie Guixian; Miao Zhiwei;
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作者单位

Nankai Univ Coll Chem State Key Lab Weijin Rd 94 Tianjin 300071 Peoples R China;

Nankai Univ Coll Chem State Key Lab Weijin Rd 94 Tianjin 300071 Peoples R China;

Nankai Univ Coll Chem State Key Lab Weijin Rd 94 Tianjin 300071 Peoples R China;

Hunan Agr Univ Coll Resources &

Environm Changsha 410128 Hunan Peoples R China;

Nankai Univ Coll Chem State Key Lab Weijin Rd 94 Tianjin 300071 Peoples R China;

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正文语种 eng
中图分类化学;
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1. K3PO4-promoted domino reactions: diastereoselective synthesis of trans-2,3-dihydrobenzofurans from salicyl N-tert-butanesulfinyl imines and sulfur ylides [J] . Zhang Minxuan, Lu Tianyu, Zhao Yun, RSC Advances . 2019,第21期

机译：K3PO4-促进的多米诺反应：从水杨基N-叔丁沙磺酰亚胺和硫酰胺中的反式选择性合成反式-2,3-二氢苯并呋喃
2. Domino reaction for the chemo- and stereoselective synthesis of trans-2,3-dihydrobenzofurans from N-thiophosphinyl imines and sulfur ylides [J] . Xie P., Wang L., Yang L., The Journal of Organic Chemistry . 2011,第19期

机译：从N-硫代次膦亚胺和硫酰化物化学合成和立体选择反式2,3-二氢苯并呋喃的多米诺反应
3. Phosphine-catalyzed domino reaction: Highly stereoselective synthesis of trans-2,3-dihydrobenzofurans from salicyl n-thiophosphinyl imines and allylic carbonates [J] . Xie P., Huang Y., Chen R. Organic letters . 2010,第17期

机译：膦催化的多米诺反应：由水杨基正硫代次膦亚胺和烯丙基碳酸酯高度立体选择性地合成反式2,3-二氢苯并呋喃
4. SYNTHESIS OF 2,3-DIHYDROBENZOFURAN DERIVATIVES VIA ELECTRON TRANSFER REACTION CATALYZED BY IRON(III)-SALT IN AN IONIC LIQUID SOLVENT SYSTEM [C] . Toshiyuki Itoh, Hiroyuki Uehara, Kimio Kawai, Proceedings vol.2004-10; International Manuel M. Baizer Symposium in Honor of Dennis H. Evans and Masao Tokuda and Meeting of the Electrochemical Society; 20040509-14; San Antonio,TX(US) . 2004

机译：离子液体溶剂中铁（III）-盐催化的电子转移反应合成2,3-二羟基苯并呋喃衍生物
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. Synthesis of Chiral Aziridines through Decarboxylative Generation of Sulfur Ylides and their Reaction with Chiral Sulfinyl Imines [O] . David C. Forbes, Sampada V. Bettigeri, Sejal R. Amin, -1

机译：硫叶立德的脱羧合成手性氮丙啶及其与手性亚磺酰基亚胺的反应
7. Diastereoselective One-Pot Synthesis of Oxazolines Using Sulfur Ylides and Acyl Imines [O] . -1

机译：使用硫酰胺和酰基亚胺的恶唑啉植物的非对映选择性的一次性合成
8. Synthesis and Reactions of Highly Electrophilic Imines Containing the N-Cyano Group. [R] . Ramezanian, M., Padias, A. B., Saeva, F. D., 1990

机译：含氰基的高亲电子的合成及反应。

K3PO4-promoted domino reactions: diastereoselective synthesis of trans-2,3-dihydrobenzofurans from salicyl N-tert-butanesulfinyl imines and sulfur ylides

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