Enantioselective Reactions of 2-Sulfonylalkyl Phenols with Allenic Esters: Dynamic Kinetic Resolution and [4+2] Cycloaddition Involving ortho-Quinone Methide Intermediates
文献类型：期刊论文
| 作者 | Li, Can1; Wang, Kai1,2; Chen, Ping1,2; Guo, Wengang1; Liu, Xianghui1,2; Liu, Yan1 |
| 刊名 | ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
 |
| 出版日期 | 2017-03-20 |
| 卷号 | 56期号:13页码:3689-3693 |
| ISSN号 | 1433-7851 |
| 关键词 | Benzylic Sulfones Chromans Cycloaddition Dynamic Kinetic Resolution Ortho-quinone Methides |
| DOI | 10.1002/ange.201700250 |
| 文献子类 | Article |
| 英文摘要 | We report herein a dynamic kinetic resolution (DKR) involving ortho-quinone methide (o-QM) intermediates. In the presence of Et3N and the cinchonine-derived nucleophilic catalyst D, the DKR of 2-sulfonylalkyl phenols with allenic esters afforded chiral benzylic sulfones in 57-79% yield with good to excellent enantioselectivity (85-95% ee). Furthermore, with 2-(tosylmethyl) sesamols or 2-(tosylmethyl)-naphthols, from which stable o-QM substrates can be generated, a formal [4+2] cycloaddition delivered 4-aryl- or alkyl-substituted chromans with excellent enantioselectivity (88-97% ee). |
| WOS关键词 | HIGHLY FUNCTIONALIZED TETRAHYDROPYRIDINES ; CATALYTIC ASYMMETRIC-SYNTHESIS ; O-HYDROXYBENZYL ALCOHOLS ; BRONSTED ACID CATALYSIS ; BAYLIS-HILLMAN REACTION ; IN-SITU ; CONJUGATE ADDITION ; ALLYLIC SULFONES ; ALLENOATES ; ANNULATIONS |
| WOS研究方向 | Chemistry |
| 语种 | 英语 |
| 出版者 | WILEY-V C H VERLAG GMBH |
| WOS记录号 | WOS:000397339400046 |
| 源URL | [http://cas-ir.dicp.ac.cn/handle/321008/169454]  |
| 专题 | 大连化学物理研究所_中国科学院大连化学物理研究所 |
| 通讯作者 | Li, Can; Liu, Yan |
| 作者单位 | 1.Chinese Acad Sci, State Key Lab Catalysis, Dalian Inst Chem Phys, 457 Zhongshan Rd, Dalian 116023, Peoples R China 2.Grad Univ, Chinese Acad Sci, Beijing 100049, Peoples R China |
| 推荐引用方式 GB/T 7714 | Li, Can,Wang, Kai,Chen, Ping,et al. Enantioselective Reactions of 2-Sulfonylalkyl Phenols with Allenic Esters: Dynamic Kinetic Resolution and [4+2] Cycloaddition Involving ortho-Quinone Methide Intermediates[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,2017,56(13):3689-3693. |
| APA | Li, Can,Wang, Kai,Chen, Ping,Guo, Wengang,Liu, Xianghui,&Liu, Yan.(2017).Enantioselective Reactions of 2-Sulfonylalkyl Phenols with Allenic Esters: Dynamic Kinetic Resolution and [4+2] Cycloaddition Involving ortho-Quinone Methide Intermediates.ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,56(13),3689-3693. |
| MLA | Li, Can,et al."Enantioselective Reactions of 2-Sulfonylalkyl Phenols with Allenic Esters: Dynamic Kinetic Resolution and [4+2] Cycloaddition Involving ortho-Quinone Methide Intermediates".ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 56.13(2017):3689-3693. |
入库方式： OAI收割
来源：大连化学物理研究所
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