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

[1] A critical outlook and comparison of enantioselective oxidation methodologies of olefins [J].

Bonini, C ;

Righi, G .

TETRAHEDRON, 2002, 58 (25) :4981-5021

[2] Catalytic asymmetric epoxidation of alpha,beta-unsaturated ketones promoted by lanthanoid complexes [J].

Bougauchi, M ;

Watanabe, S ;

Arai, T ;

Sasai, H ;

Shibasaki, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (09) :2329-2330

[3] Remarkable ligand effect on the enantioselectivity of the chiral lanthanum complex-catalyzed asymmetric epoxidation of enones [J].

Daikai, K ;

Kamaura, M ;

Inanaga, J .

TETRAHEDRON LETTERS, 1998, 39 (40) :7321-7322

[4]

Goodman SN, 2002, ADV SYNTH CATAL, V344, P953, DOI 10.1002/1615-4169(200210)344:9<953::AID-ADSC953>3.0.CO

[5]

2-A

[6] REMOVAL OF FORMYL, ACETYL, AND BENZOYL GROUPS FROM AMIDES WITH CONVERSION INTO THE CORRESPONDING TERT-BUTYL CARBAMATES [J].

GREHN, L ;

GUNNARSSON, K ;

RAGNARSSON, U .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1985, (19) :1317-1318

[7] ENANTIOSELECTIVE CATALYTIC EPOXIDATION OF CINNAMATE ESTERS [J].

JACOBSEN, EN ;

DENG, L ;

FURUKAWA, Y ;

MARTINEZ, LE .

TETRAHEDRON, 1994, 50 (15) :4323-4334

[8] STEREOSPECIFIC REARRANGEMENT OF OPTICALLY-ACTIVE TERTIARY ALLYLIC EPOXIDES TO GIVE OPTICALLY-ACTIVE QUATERNARY ALDEHYDES - SYNTHESIS OF ALPHA-ALKYL AMINO ALDEHYDES AND ACIDS [J].

JUNG, ME ;

DAMICO, DC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (28) :7379-7388

[9] Catalytic asymmetric epoxidation of α,β-unsaturated esters using an yttrium-biphenyidiol complex [J].

Kakei, H ;

Tsuji, R ;

Ohshima, T ;

Shibasaki, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (25) :8962-8963

[10] Oligopeptides as catalysts for asymmetric epoxidation [J].

Kelly, DR ;

Roberts, SM .

BIOPOLYMERS, 2006, 84 (01) :74-89

← 1 2 3 4 →