Highly enantioselective addition of diphenylzinc to aliphatic and aromatic aldehydes catalyzed by a readily available H8-binol derivative

被引：65

作者：

Qin, YC ^{[1
]}

Pu, L ^{[1
]}

机构：

[1] Univ Virginia, Dept Chem, Charlottesville, VA 22904 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2006年 / 45卷 / 02期

关键词：

alcohols; aldehydes; asymmetric synthesis; nucleophilic addition; zinc;

D O I：

10.1002/anie.200503206

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) All sorts of aldehydes 2 (R = aryl, vinyl, branched, and linear alkyl) undergo the highly enantioselective addition of diphenylzinc (1) in the presence of catalytic (S)-4 to give α-substituted benzyl alcohols 3 in high yields. In contrast to previous catalysts, no additive is required, the reaction is carried out at room temperature, and the reaction is equally effective with linear aldehydes. © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：273 / 277

页数：5

共 37 条

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[22] Highly enantioselective alkynylzinc addition to aromatic aldehydes catalyzed by self-assembled titanium catalysts
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1600, American Chemical Society (124):
[23] Enantioselective addition of diethylzinc to aromatic aldehydes catalyzed by Ti(IV) complexes of C2-symmetrical chiral BINOL derivatives
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[24] Synthesis of a C1 symmetric BINOL-terpyridine ligand and highly enantioselective methyl propiolate addition to aromatic aldehydes
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[25] Application of a Heterogeneous Chiral Titanium Catalyst Derived from Silica-Supported 3-Aryl H8-BINOL to Enantioselective Alkylation and Arylation of Aldehydes
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[26] New Chiral Monophosphite Ligands Containing BINOL and/or H8-BINOL Bearing Adamantyl Substituents: Effect of Ligand Scaffold on the Enantioselective 1,4-Conjugate Addition of Diethylzinc to Cyclic Enones
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[27] Synthesis of a Newly Modified Poly-H8-BINOL Ligand and Its Applications in the Asymmetric Addition of Triethylaluminium to Aromatic Aldehydes
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[28] Synthesis of a newly modified poly-H8-BINOL ligand and its applications in the asymmetric addition of triethylaluminium to aromatic aldehydes
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Chemical Research in Chinese Universities, 2017, 33 : 742 - 745
[29] Enantioselective 1,4-addition of aliphatic Grignard reagents to enones catalyzed by readily available copper(I) thiolates derived from TADDOL - Preliminary communication
Seebach, D
Jaeschke, G
Pichota, A
Audergon, L
HELVETICA CHIMICA ACTA, 1997, 80 (08) : 2515 - 2519
[30] CHIRAL N,N-DIALKYLNOREPHEDRINES AS CATALYSTS OF THE HIGHLY ENANTIOSELECTIVE ADDITION OF DIALKYLZINCS TO ALIPHATIC AND AROMATIC-ALDEHYDES - THE ASYMMETRIC-SYNTHESIS OF SECONDARY ALIPHATIC AND AROMATIC ALCOHOLS OF HIGH OPTICAL PURITY
SOAI, K
YOKOYAMA, S
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