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J Org Chem. 2007 Jan 5;72(1):97-101. doi: 10.1021/jo061769i.
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J Am Chem Soc. 2006 Aug 30;128(34):10996-7. doi: 10.1021/ja062711o.
3
Dinuclear Zn-catalyzed asymmetric alkynylation of unsaturated aldehydes.双核锌催化的不饱和醛的不对称炔基化反应
J Am Chem Soc. 2006 Jan 11;128(1):8-9. doi: 10.1021/ja054871q.
4
Highly enantioselective synthesis of gamma-hydroxy-alpha,beta-acetylenic esters by asymmetric alkyne addition to aldehydes.通过醛的不对称炔烃加成反应实现γ-羟基-α,β-炔基酯的高度对映选择性合成。
Angew Chem Int Ed Engl. 2005 Dec 16;45(1):122-5. doi: 10.1002/anie.200500469.
5
Asymmetric alkynylation of aldehydes catalyzed by an In(III)/BINOL complex.铟（III）/联萘酚配合物催化的醛的不对称炔基化反应
J Am Chem Soc. 2005 Oct 12;127(40):13760-1. doi: 10.1021/ja053946n.
6
Synthesis of C3-symmetric tris(beta-hydroxy amide) ligands and their Ti(IV) complex-catalyzed enantioselective alkynylation of aldehydes.C3对称三（β-羟基酰胺）配体的合成及其Ti(IV)配合物催化的醛的对映选择性炔基化反应
Org Lett. 2005 May 26;7(11):2081-4. doi: 10.1021/ol050047v.
7
Enantioselective alkynylation of aldehydes catalyzed by [2.2]paracyclophane-based ligands.基于[2.2]对环芳烷配体催化的醛的对映选择性炔基化反应。
Org Lett. 2004 Jun 24;6(13):2113-6. doi: 10.1021/ol049596b.
8
Highly enantioselective addition of phenylacetylene to aldehydes catalyzed by a camphorsulfonamide ligand.樟脑磺酰胺配体催化苯乙炔对醛的高度对映选择性加成反应。
Org Lett. 2004 Apr 15;6(8):1193-5. doi: 10.1021/ol036418u.
9
Highly enantioselective alkyne additions to aldehydes in the presence of 1,1'-bi-2-naphthol and hexamethylphosphoramide.在1,1'-联二萘酚和六甲基磷酰胺存在下，醛与炔烃的高度对映选择性加成反应。
Proc Natl Acad Sci U S A. 2004 Apr 13;101(15):5417-20. doi: 10.1073/pnas.0307136101. Epub 2004 Mar 16.
10
Highly enantioselective addition of phenylacetylene to aldehydes catalyzed by a beta-sulfonamide alcohol-titanium complex.
Angew Chem Int Ed Engl. 2003 Dec 1;42(46):5747-9. doi: 10.1002/anie.200352572.

带有庞大3,3'-叔烷基取代基的1,1'-联萘配体用于不对称炔烃加成到芳香醛的反应

1,1'-Binaphthyl Ligands with Bulky 3,3'-Tertiaryalkyl Substituents for the Asymmetric Alkyne Addition to Aromatic Aldehydes.

作者信息

Wang Qin, Chen Shan-Yong, Yu Xiao-Qi, Pu Lin

机构信息

Department of Chemistry, Key Laboratory of Green Chemistry and Technology (Ministry of Education), Sichuan University, Chengdu, Sichuan 610064, P. R. China.

出版信息

Tetrahedron. 2007 May 21;63(21):4422-4428. doi: 10.1016/j.tet.2007.03.080.

DOI:10.1016/j.tet.2007.03.080
PMID:19081823
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC2597862/
Abstract

The BINOL ligand (R)-2 that contains bulky 3,3'-tertiaryalkyl groups shows improved catalytic properties than the previously reported 3,3'-substituted BINOL ligands in the asymmetric alkyne addition to aromatic aldehydes. It can catalyze the phenylacetylene addition to aromatic aldehydes with high enantioselectivity (86 - 94% ee) and good yields without using Ti(O(i)Pr)(4) and a Lewis base additive. The catalytic properties of several analogs of (R)-2 in the asymmetric alkyne addition to aldehydes have also been studied. .

摘要

含有庞大的3,3'-叔烷基的联萘酚配体（R）-2在芳族醛的不对称炔烃加成反应中比先前报道的3,3'-取代的联萘酚配体表现出更好的催化性能。它可以在不使用Ti（O（i）Pr）（4）和路易斯碱添加剂的情况下，以高对映选择性（86-94％ee）和良好的产率催化苯乙炔与芳族醛的加成反应。还研究了（R）-2的几种类似物在醛的不对称炔烃加成反应中的催化性能。