Asymmetric Synthesis of 1,3-Butadienyl-2-carbinols by the Homoallenylboration of Aldehydes with a Chiral Phosphoric Acid Catalyst
文献类型：期刊论文
| 作者 | Huang, Yiyong; Yang, Xing; Lv, Zongchao; Cai, Chen; Kai, Cheng; Pei, Yong; Feng, Yu |
| 刊名 | ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
 |
| 出版日期 | JUN 15 2015 |
| 卷号 | 54期号:25页码:7299-7302 |
| 英文摘要 | Asymmetric C(sp) C(sp(2)) bond formation to give enantiomerically enriched 1,3-butadienyl-2-carbinols occurred through a homoallenylboration reaction between a 2,3-dienylboronic ester and aldehydes under the catalysis of a chiral phosphoric acid (CPA). A diverse range of enantiomerically enriched butadiene-substituted secondary alcohols with aryl, heterocyclic, and aliphatic substituents were synthesized in very high yield with high enantioselectivity. Preliminary density functional theory (DFT) calculations suggest that the reaction proceeds via a cyclic six-membered chairlike transition state with essential hydrogen-bond activation in the allene reagent. The catalytic reaction was amenable to the gram-scale synthesis of a chiral alkyl butadienyl adduct, which was converted into an interesting optically pure compound bearing a benzo-fused spirocyclic cyclopentenone framework. |
| 源URL | [http://ir.iccas.ac.cn/handle/121111/38675]  |
| 专题 | 化学研究所_其它 |
| 推荐引用方式 GB/T 7714 | Huang, Yiyong,Yang, Xing,Lv, Zongchao,et al. Asymmetric Synthesis of 1,3-Butadienyl-2-carbinols by the Homoallenylboration of Aldehydes with a Chiral Phosphoric Acid Catalyst[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,JUN ,54(25):7299-7302. |
| APA | Huang, Yiyong.,Yang, Xing.,Lv, Zongchao.,Cai, Chen.,Kai, Cheng.,...&Feng, Yu.(JUN ).Asymmetric Synthesis of 1,3-Butadienyl-2-carbinols by the Homoallenylboration of Aldehydes with a Chiral Phosphoric Acid Catalyst.ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,54(25),7299-7302. |
| MLA | Huang, Yiyong,et al."Asymmetric Synthesis of 1,3-Butadienyl-2-carbinols by the Homoallenylboration of Aldehydes with a Chiral Phosphoric Acid Catalyst".ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 54.25(JUN ):7299-7302. |
入库方式： OAI收割
来源：化学研究所
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