Palladium-indium iodide-mediated allylation and propargylation of glyoxylic oxime ether and hydrazone: The role of water in directing the diastereoselective allylation

被引：62

作者：

Miyabe, H

Yamaoka, Y

Naito, T

Takemoto, Y ^{[1
]}

机构：

[1] Kyoto Univ, Grad Sch Pharmaceut Sci, Sakyo Ku, Kyoto 6068501, Japan

[2] Kobe Pharmaceut Univ, Kobe, Hyogo 6588558, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2004年 / 69卷 / 04期

关键词：

D O I：

10.1021/jo035442i

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Allylation and propargylation of glyoxylic oxime ether in the presence of a catalytic amount of palladium(0) complex and indium(I) iodide were studied. Excellent diastereoselectivities in allylation were achieved in the presence of water, although low diastereoselectivities were observed in the absence of water. Propargylation of glyoxylic oxime ether proceeded with good diastereoselectivities in the presence of LiBr or LiCl.

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页码：1415 / 1418

页数：4

相关论文

共 42 条

[11] Asymmetric synthesis of L-azetidine-2-carboxylic acid and 3-substituted congeners - Conformationally constrained analogs of phenylalanine, naphthylalanine, and leucine [J].

Hanessian, S ;

Bernstein, N ;

Yang, RY ;

Maguire, R .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1999, 9 (10) :1437-1442

[12]

Hanessian S, 1999, ANGEW CHEM INT EDIT, V38, P3160

[13] The asymmetric synthesis of allylglycine and other unnatural alpha-amino acids via zinc-mediated allylation of oximes in aqueous media [J].

Hanessian, S ;

Yang, RY .

TETRAHEDRON LETTERS, 1996, 37 (30) :5273-5276

[14] Allylic-type diindium reagents. Reactivity toward electrophiles and cascade coupling reactions with imines [J].

Hirashita, T ;

Hayashi, Y ;

Mitsui, K ;

Araki, S .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (04) :1309-1313

[15] Palladium-indium-mediated arylative cyclization of allenyl-aldehydes and -ketones [J].

Kang, SK ;

Lee, SW ;

Jung, JY ;

Lim, Y .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (12) :4376-4379

[16] Indium-mediated diastereoselective allylation reactions:: preparation of α-hydroxy and α-amino acids [J].

Lee, JG ;

Choi, KI ;

Pae, AN ;

Koh, HY ;

Kang, YH ;

Cho, YS .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, (10) :1314-1317

[17]

Lee K, 2002, ANGEW CHEM INT EDIT, V41, P3901, DOI 10.1002/1521-3773(20021018)41:20<3901::AID-ANIE3901>3.0.CO

[18]

2-S

[19] Organic syntheses using indium-mediated and catalyzed reactions in aqueous media [J].

Li, CJ ;

Chan, TH .

TETRAHEDRON, 1999, 55 (37) :11149-11176

[20] A new mechanistic proposal for the origin of α-homoallylic alcohols in indium-mediated allylation reactions in water [J].

Loh, TP ;

Tan, KT ;

Hu, QY .

TETRAHEDRON LETTERS, 2001, 42 (49) :8705-8708

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