(N,N-Diisopropylcarbamoyloxy)-methyl p-tolyl sulfone: preparation and application for the syntheses of 1,2-diols
文献类型：期刊论文
| 作者 | Ma, Lu1,2; Zhao, Dongmei2; Chen, Lin1; Wang, Xin1 ; Chen, Yue-Lei1; Shen, Jingkang1
|
| 刊名 | TETRAHEDRON
 |
| 出版日期 | 2012-10-21 |
| 卷号 | 68期号:42页码:8704-8711 |
| 关键词 | Nucleophilic addition Aldehydes N,N-Diisopropylcarbamoyl Regioselective protection 1,2-Diols |
| ISSN号 | 0040-4020 |
| DOI | 10.1016/j.tet.2012.08.025 |
| 文献子类 | Article |
| 英文摘要 | 1-(N,N-Diisopropylcarbamoyloxy)-1-tosyl-methane (CbOCH2Ts, Cb=N,N-diisopropylcarbamoyl) was readily prepared from p-ToISH, paraformaldehyde and CbCl. With the dual activation of CbO- and Ts-substitutions, deprotonation of CbOCH2Ts could be effected not only by n-BuLi, but also by Grignard reagents. Upon deprotonation, the title compound adds to various carbonyl structures. By choosing proper organometallic reagents for consecutive steps, the addition intermediate undergoes in situ conversions to efficiently yield regioselectively O-Cb protected and unprotected 1,2-diols. (C) 2012 Elsevier Ltd. All rights reserved. |
| WOS关键词 | CHIRAL HOMOENOLATE REAGENTS ; NUCLEOPHILIC ALKENOYLATION ; ASYMMETRIC-SYNTHESIS ; DIHYDROXYLATION ; ACID ; DEPROTONATION ; DERIVATIVES ; ALKENES |
| 资助项目 | National Natural Science Foundation of China[81102306] |
| WOS研究方向 | Chemistry |
| 语种 | 英语 |
| WOS记录号 | WOS:000309252100003 |
| 出版者 | PERGAMON-ELSEVIER SCIENCE LTD |
| 源URL | [http://119.78.100.183/handle/2S10ELR8/277907]  |
| 专题 | 药物化学研究室 |
| 通讯作者 | Chen, Yue-Lei |
| 作者单位 | 1.Chinese Acad Sci, Shanghai Inst Mat Med, Shanghai 201203, Peoples R China; 2.Shenyang Pharmaceut Univ, Shenyang 110016, Peoples R China |
| 推荐引用方式 GB/T 7714 | Ma, Lu,Zhao, Dongmei,Chen, Lin,et al. (N,N-Diisopropylcarbamoyloxy)-methyl p-tolyl sulfone: preparation and application for the syntheses of 1,2-diols[J]. TETRAHEDRON,2012,68(42):8704-8711. |
| APA | Ma, Lu,Zhao, Dongmei,Chen, Lin,Wang, Xin,Chen, Yue-Lei,&Shen, Jingkang.(2012).(N,N-Diisopropylcarbamoyloxy)-methyl p-tolyl sulfone: preparation and application for the syntheses of 1,2-diols.TETRAHEDRON,68(42),8704-8711. |
| MLA | Ma, Lu,et al."(N,N-Diisopropylcarbamoyloxy)-methyl p-tolyl sulfone: preparation and application for the syntheses of 1,2-diols".TETRAHEDRON 68.42(2012):8704-8711. |
入库方式： OAI收割
来源：上海药物研究所
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