Highly Enantioselective Addition of Terminal Alkynes to Aldehydes Catalyzed by a New Chiral β-Sulfonamide Alcohol/Ti(OiPr)4/Et2Zn/R3N Catalyst System

被引：25

作者：

Qiu, Li ^{[1
,2
]}

Wang, Quan ^{[2
]}

Lin, Li ^{[2
]}

Liu, Xiaodong ^{[2
]}

Jiang, Xianxing ^{[2
]}

Zhao, Qingyang ^{[2
]}

Hu, Guowen ^{[2
]}

Wang, Rui ^{[1
,2
]}

机构：

[1] Chinese Acad Sci, Lanzhou Inst Chem Phys, State Key Lab Oxo Synth & Select Oxidat, Lanzhou 730000, Peoples R China

[2] Lanzhou Univ, Inst Biochem & Mol Biol, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China

来源：

CHIRALITY | 2009年 / 21卷 / 02期

关键词：

enantioselective addition; sulfonamide alcohol; tertiary amine base; terminal alkynes; aldehydes; IN-SITU GENERATION; ASYMMETRIC ALKYNYLATION; AROMATIC-ALDEHYDES; GAMMA-HYDROXY-ALPHA; BETA-ACETYLENIC ESTERS; PHENYLACETYLENE ADDITION; ALKYNYLZINC ADDITION; TITANIUM COMPLEXES; MILD; ALCOHOLS; LIGANDS;

D O I：

10.1002/chir.20583

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A new catalytic system, generated from the readily available and inexpensive P-sulfonamide alcohol L*, Ti((OPr)-Pr-i)(4), Et2Zn, and tertiary amine base (R3N), effectively catalyzes the enantioselective addition of various terminal alkynes including some quite challenging alkynes to aldehydes in good yields and excellent enantioselectivities. Up to 96% yield and >99% enantioselectivity were achieved with the use of N,N-diisoproylethylamine (DIPEA) as an additive in this asymmetric addition. Chirality 21:316-323, 2009. (C) 2008 Wiley-Liss, Inc.

引用

页码：316 / 323

页数：8

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