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Asymmetric Synthesis of 1,3-Butadienyl-2-carbinols by the Homoallenylboration of Aldehydes with a Chiral Phosphoric Acid Catalyst
Huang, Yiyong; Yang, Xing; Lv, Zongchao; Cai, Chen; Kai, Cheng; Pei, Yong; Feng, Yu
JUN 15 2015
Source PublicationANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume54Issue:25Pages:7299-7302
AbstractAsymmetric 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.
Document Type期刊论文
Identifierhttp://ir.iccas.ac.cn/handle/121111/38675
Collection其它
Recommended Citation
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.
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