Nickel complexes from α-amino amides as efficient catalysts for the enantioselective Et2Zn addition to benzaldehyde

被引：43

作者：

Burguete, MI ^{[1
]}

Collado, M ^{[1
]}

Escorihuela, J ^{[1
]}

Galindo, F ^{[1
]}

García-Verdugo, E ^{[1
]}

Luis, SV ^{[1
]}

Vicent, MJ ^{[1
]}

机构：

[1] Univ Jaume 1, Dept Inorgan & Organ Chem, ESTCE, E-12080 Castellon de La Plana, Spain

来源：

TETRAHEDRON LETTERS | 2003年 / 44卷 / 36期

关键词：

D O I：

10.1016/S0040-4039(03)01705-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Ni2+ complexes derived from simple alpha-amino amides catalyze very efficiently the addition of Et2Zn to benzaldehyde, giving (S)-1-phenylethanol as the major isomer in most cases (94% yield, 97% ee for R=Bn). The nature of the substituent on the amide nitrogen atom seems to play a key role in determining the asymmetric induction observed. (C) 2003 Elsevier Ltd. All rights reserved.

引用

页码：6891 / 6894

页数：4

共 58 条

[21] Amino acids and peptides as asymmetric organocatalysts [J].

Jarvo, ER ;

Miller, SJ .

TETRAHEDRON, 2002, 58 (13) :2481-2495

[22] Enantioselective additions of diethylzinc and diphenylzinc to aldehydes using 2-dialkyl-aminomethyl-2′-hydroxy-1,1′-binaphthyls [J].

Ko, DH ;

Kim, KH ;

Ha, DC .

ORGANIC LETTERS, 2002, 4 (21) :3759-3762

[23] ASYMMETRIC ALDOL REACTION BETWEEN ACHIRAL SILYL ENOL ETHERS AND ACHIRAL ALDEHYDES BY USE OF A CHIRAL PROMOTER SYSTEM [J].

KOBAYASHI, S ;

UCHIRO, H ;

FUJISHITA, Y ;

SHIINA, I ;

MUKAIYAMA, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (11) :4247-4252

[24] CHIRAL LEWIS-ACID-CONTROLLED SYNTHESIS OF BOTH DIASTEREOMERS - ENANTIOSELECTIVE SYNTHESIS OF BOTH SYN-2,3-DIHYDROXY AND ANTI-2,3-DIHYDROXY ESTER DERIVATIVES FROM THE SAME STARTING MATERIALS VIA ASYMMETRIC ALDOL REACTIONS BY CHOICE OF CHIRAL LIGANDS [J].

KOBAYASHI, S ;

HAYASHI, T .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (05) :1098-1099

[25] Ti-mediated addition of diethylzinc to benzaldehyde. The effect of chiral additives [J].

Lake, F ;

Moberg, C .

TETRAHEDRON-ASYMMETRY, 2001, 12 (05) :755-760

[26] The application of chiral aminonaphthols in the enantioselective addition of diethylzinc to aryl aldehydes [J].

Liu, DX ;

Zhang, LC ;

Wang, Q ;

Da, CS ;

Xin, ZQ ;

Wang, R ;

Choi, MCK ;

Chan, ASC .

ORGANIC LETTERS, 2001, 3 (17) :2733-2735

[27]

Lucet D, 1998, ANGEW CHEM INT EDIT, V37, P2581, DOI 10.1002/(SICI)1521-3773(19981016)37:19<2580::AID-ANIE2580>3.0.CO

[28]

2-L

[29] Asymmetric molybdenum(0)-catalyzed allylic substitution [J].

Malkov, AV ;

Spoor, P ;

Vinader, V ;

Kocovsky, P .

TETRAHEDRON LETTERS, 2001, 42 (03) :509-512

[30] BIOTIN BIOSYNTHESIS [J].

MARQUET, A .

PURE AND APPLIED CHEMISTRY, 1993, 65 (06) :1249-1252

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