Lanthanoid triflates catalyzed reaction of a silyl ynolate with aldimines

被引：27

作者：

Shindo, M ^{[1
]}

Oya, S ^{[1
]}

Sato, Y ^{[1
]}

Shishido, K ^{[1
]}

机构：

[1] Univ Tokushima, Inst Med Resources, Tokushima 7708505, Japan

来源：

HETEROCYCLES | 2000年 / 52卷 / 02期

关键词：

D O I：

10.3987/COM-99-S70

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A silyl ynolate, prepared from alpha,alpha-dibromo ester in one-pot, reacts with N-(p-methoxyphenyl)aldimines in the presence of a catalytic amount of lanthanoid triflates to provide alpha,beta-unsaturated amides with high E selectivity.

引用

页码：545 / 548

页数：4

共 17 条

[1] A new reaction of imines with alkynyl sulfides affording alpha,beta-unsaturated thioimidates [J].

Ishitani, H ;

Nagayama, S ;

Kobayashi, S .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (06) :1902-1903

[2]

KOBAYASHI S, 1994, SYNLETT, P689

[3] A NOVEL MANNICH-TYPE REACTION IN AQUEOUS-MEDIA - LANTHANIDE TRIFLATE-CATALYZED CONDENSATION OF ALDEHYDES, AMINES AND VINYL ETHERS FOR THE SYNTHESIS OF BETA-AMINO KETONES [J].

KOBAYASHI, S ;

ISHITANI, H .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (13) :1379-1379

[4]

KOBAYASHI S, 1995, SYNLETT, P233

[5] Aldehydes vs aldimines. Unprecedented aldimine-selective nucleophilic additions in the coexistence of aldehydes using a lanthanide salt as a Lewis acid catalyst [J].

Kobayashi, S ;

Nagayama, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (42) :10049-10053

[6] Aldehydes vs aldimines. Unprecedented reactivity in their enolate addition reactions [J].

Kobayashi, S ;

Nagayama, S .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (02) :232-233

[7] LANTHANIDE TRIFLATES AS WATER-TOLERANT LEWIS-ACIDS - ACTIVATION OF COMMERCIAL FORMALDEHYDE SOLUTION AND USE IN THE ALDOL REACTION OF SILYL ENOL ETHERS WITH ALDEHYDES IN AQUEOUS-MEDIA [J].

KOBAYASHI, S ;

HACHIYA, I .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (13) :3590-3596

[8] TRISUBSTITUTED OLEFINS VIA ESTER-DERIVED (SILYLOXY)ACETYLENES - A HIGHLY STEREOSELECTIVE ALTERNATIVE TO THE HORNER-WADSWORTH-EMMONS REACTION [J].

KOWALSKI, CJ ;

SAKDARAT, S .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (07) :1977-1979

[9] YNOL SILYL ETHERS VIA O-SILYLATION OF ESTER-DERIVED YNOLATE ANIONS [J].

KOWALSKI, CJ ;

LAL, GS ;

HAQUE, MS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (22) :7127-7128

[10] Experimental evidence for a [2+2] mechanism in the Lewis acid-promoted formation of α,β-unsaturated esters from ethoxyacetylene and aldehydes.: Synthesis and characterisation of 4-ethoxyoxetes. [J].

Oblin, M ;

Parrain, JL ;

Rajzmann, M ;

Pons, JM .

CHEMICAL COMMUNICATIONS, 1998, (16) :1619-1620

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