First evidence for the formation of a geminal dizinc carbenoid: A highly stereoselective synthesis of 1,2,3-substituted cyclopropanes

被引：45

作者：

Charette, AB ^{[1
]}

Gagnon, A ^{[1
]}

Fournier, JF ^{[1
]}

机构：

[1] Univ Montreal, Dept Chim, Montreal, PQ H3C 3J7, Canada

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2002年 / 124卷 / 03期

关键词：

D O I：

10.1021/ja017230d

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Significant amounts of novel gem-dizinc carbenoids (RZnCHIZnR) are formed when diethylzinc is mixed with iodoform in CH2Cl2 at 0 °C. This reagent was shown to be effective in the cyclopropanation of butenediol derivatives to generate a cyclopropylzinc intermediate that could be trapped with a variety of electrophiles. 1,2,3-Substituted cyclopropane derivatives are formed with excellent diastereoselectivities by using this simple procedure. Copyright © 2002 American Chemical Society.

引用

页码：386 / 387

页数：2

共 24 条

[11] SYNTHESIS AND REACTIVITY TOWARD ACYL CHLORIDES AND ENONES OF THE NEW HIGHLY FUNCTIONALIZED COPPER REAGENTS RCU(CN)ZNI [J].

KNOCHEL, P ;

YEH, MCP ;

BERK, SC ;

TALBERT, J .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (10) :2390-2392

[12] Synthesis and reactivity of sp(3)-geminated organodimetallics [J].

Marek, I ;

Normant, JF .

CHEMICAL REVIEWS, 1996, 96 (08) :3241-3267

[13] Iodocyclopropanes as versatile intermediates for the synthesis of substituted cyclopropanes [J].

Martin, SF ;

Dwyer, MP .

TETRAHEDRON LETTERS, 1998, 39 (12) :1521-1524

[14] Bis(iodozincio)methane - preparation, structure, and reaction [J].

Matsubara, S ;

Oshima, K ;

Utimoto, K .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2001, 617 (01) :39-46

[15] REACTIONS OF IODOCARBENOID OF ZINC .2. IODOCYCLOPROPANATION OF OLEFINS WITH DIETHYLZINC AND IODOFORM [J].

MIYANO, S ;

HASHIMOT.H .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1974, 47 (06) :1500-1503

[16] CARBON-CARBON BOND-FORMING REACTIONS OF ZINC HOMOENOLATE OF ESTERS - A NOVEL 3-CARBON NUCLEOPHILE WITH GENERAL SYNTHETIC UTILITY [J].

NAKAMURA, E ;

AOKI, S ;

SEKIYA, K ;

OSHINO, H ;

KUWAJIMA, I .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (26) :8056-8066

[17] CARBOMETALATION OF CYCLOPROPENE - LIGAND-INDUCED ENANTIOSELECTIVE ALLYLZINCATION [J].

NAKAMURA, M ;

ARAI, M ;

NAKAMURA, E .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (03) :1179-1180

[18]

NISHIMURA J, 1971, CHEM COMMUN, P1375

[19] 1,1-dimetallic reagents for the elaboration of stereoselectively di- or trisubstituted linear substrates [J].

Normant, JF .

ACCOUNTS OF CHEMICAL RESEARCH, 2001, 34 (08) :640-644

[20] SYNTHESIS OF VINYLCYCLOPROPANES VIA PALLADIUM-CATALYZED COUPLING OF CYCLOPROPYLZINC HALIDES WITH VINYL IODIDES - TOTAL SYNTHESES OF (+/-)-PREZIZANOL AND (+/-)-PREZIZAENE [J].

PIERS, E ;

JEAN, M ;

MARRS, PS .

TETRAHEDRON LETTERS, 1987, 28 (43) :5075-5078

← 1 2 3 →