Catalytic asymmetric epoxidation of α-methyl α,β-unsaturated anilides as ester surrogates

被引：12

作者：

Chen, Zhihua ^{[1
]}

Morimoto, Hiroyuki ^{[1
]}

Matsunaga, Shigeki ^{[1
]}

Shibasaki, Masakatsu ^{[1
]}

机构：

[1] Univ Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, Tokyo 1130033, Japan

来源：

SYNLETT | 2006年 / 20期

关键词：

asymmetric catalysis; epoxide; anilide; BINOL; rare-earth metal; ALDEHYDES; COMPLEX; AMIDES; ACID;

D O I：

10.1055/s-2006-956491

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Catalytic asymmetric epoxidation of a-methyl alpha,beta-unsaturated carboxylic acid derivatives was achieved using anilide as a template. The Pr(Oi-Pr)(3)-6,6'-Ph-BINOL complex (10 mol%) with a Ph3P(O) (30 mol%) additive promoted the epoxidation of anilides in up to 99% yield and 88% ee. For alpha-methyl-beta-Ph alpha,beta-unsaturated anilide, the Gd(Oi-Pr)(3)-6,6'-I-BINOL complex (10 mol%) with Ar3P(O) (30 mol%, Ar = 4-methoxyphenyl) was suitable, giving epoxide in 87% yield and 78% ee.

引用

页码：3529 / 3532

页数：4

共 32 条

[11] Sequential Wittig olefination-catalytic asymmetric epoxidation with reuse of waste Ph3P(O):: Application of α,β-unsaturated N-acyl pyrroles as ester surrogates [J].

Kinoshita, T ;

Okada, S ;

Park, SR ;

Matsunaga, S ;

Shibasaki, M .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (38) :4680-4684

[12]

Lauret C, 2002, ALDRICHIM ACTA, V35, P47

[13] Hippuryl-α-methylphenylalanine and Hippuryl-α-methylphenyllactic acid as substrates for carboxypeptidase A.: Syntheses, kinetic evaluation and mechanistic implication [J].

Lee, M ;

Kim, DH .

BIOORGANIC & MEDICINAL CHEMISTRY, 2000, 8 (04) :815-823

[14] Asymmetric organocatalytic epoxidation of α,β-unsaturated aldehydes with hydrogen peroxide [J].

Marigo, M ;

Franzén, J ;

Poulsen, TB ;

Zhuang, W ;

Jorgensen, KA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (19) :6964-6965

[15] Catalytic asymmetric 1,4-addition reactions using α,β-unsaturated N-acylpyrroles as highly reactive monodentate α,β-unsaturated ester surrogates [J].

Matsunaga, S ;

Kinoshita, T ;

Okada, S ;

Harada, S ;

Shibasaki, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (24) :7559-7570

[16] Catalytic asymmetric epoxidation of α,β-unsaturated N-acylpyrroles as monodentate and activated ester equivalent acceptors [J].

Matsunaga, Shigeki ;

Qin, Hongbo ;

Sugita, Mari ;

Okada, Shigemitsu ;

Kinoshita, Tomofumi ;

Yamagiwa, Noriyuki ;

Shibasaki, Masakatsu .

TETRAHEDRON, 2006, 62 (28) :6630-6639

[17] Chromium- and manganese-salen promoted epoxidation of alkenes [J].

McGarrigle, EM ;

Gilheany, DG .

CHEMICAL REVIEWS, 2005, 105 (05) :1563-1602

[18] Catalytic asymmetric epoxidation of α,β-unsaturated amides:: Efficient synthesis of β-aryl α-hydroxy amides using a one-pot tandem catalytic asymmetric epoxidation-Pd-catalyzed epoxide opening process [J].

Nemoto, T ;

Kakei, H ;

Gnanadesikan, V ;

Tosaki, SY ;

Ohshima, T ;

Shibasaki, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (49) :14544-14545

[19] Catalytic asymmetric epoxidation of α,β-unsaturated carbonyl compounds [J].

Nemoto, T ;

Ohshima, T ;

Shibasaki, M .

JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2002, 60 (02) :94-105

[20] Catalytic asymmetric synthesis of α,β-epoxy esters, aldehydes, amides, and γ,δ-epoxy β-keto esters:: Unique reactivity of α,β-unsaturated carboxylic acid imidazolides [J].

Nemoto, T ;

Ohshima, T ;

Shibasaki, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (38) :9474-9475

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