Synthesis of N,N-bis(silyloxy)enamines with a functionalized double bond

被引：30

作者：

Dilman, AD ^{[1
]}

Tishkov, AA ^{[1
]}

Lyapkalo, IM ^{[1
]}

Ioffe, SL ^{[1
]}

Kachala, VV ^{[1
]}

Strelenko, YA ^{[1
]}

Tartakovsky, VA ^{[1
]}

机构：

[1] Russian Acad Sci, ND Zelinskii Organ Chem Inst, Moscow 117913, Russia

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 2000年 / 17期

关键词：

D O I：

10.1039/b004268o

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The general method for the double silylation of alpha- or beta-functionalized aliphatic nitro compounds 1 leading to regio- and stereoselective formation of N,N-bis(silyloxy)enamines 3 with a functionalized double bond is elaborated. The configuration of obtained products is determined by NMR spectroscopy.

引用

页码：2926 / 2929

页数：4

共 24 条

[11] CHELATION AS A DRIVING FORCE IN ORGANIC REACTIONS .5. PREPARATION OF ALPHA-NITRO ESTERS THROUGH CARBOXYLATION OF NITROPARAFFINS [J].

FINKBEINER, HL ;

WAGNER, GW .

JOURNAL OF ORGANIC CHEMISTRY, 1963, 28 (01) :215-&

[12]

Hesse M, 1995, SPEKTROSKOPISCHE MET, P108

[13]

HESSE M, 1995, SPEKTROSKOPISCHE MET, P161

[14]

Ioffe S. L., 1972, B ACAD SCI USSR CH, V21, p[1292, 1341]

[15] beta,beta'-functionalized N,N-divinyl-N-trimethylsilyloxyamines via silylation of beta-substituted aliphatic nitro compounds. The investigation of the mechanism of the process using selective trapping reagents. [J].

Ioffe, SL ;

Lyapkalo, IM ;

Tishkov, AA ;

Danilenko, VM ;

Strelenko, YA ;

Tartakovsky, VA .

TETRAHEDRON, 1997, 53 (38) :13085-13098

[16] Reactions of N-nitramines and their trimethylsilyl derivatives with N,N-bis(trimethylsilyloxy)enamines [J].

Ioffe, SL ;

Makarenkova, LM ;

Strelenko, YA ;

Bliznets, IV ;

Tartakovsky, VA .

RUSSIAN CHEMICAL BULLETIN, 1998, 47 (10) :1989-1991

[17]

IOFFE SL, 1986, 6 INT C ORG SYNTH MO, P48

[18] The addition of nitromethane to unsaturated esters [J].

Kohler, EP ;

Engelbrecht, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1919, 41 :764-770

[19] A NEW SYNTHESIS OF ALPHA-NITROESTERS [J].

KORNBLUM, N ;

BLACKWOOD, RK ;

POWERS, JW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1957, 79 (10) :2507-2509

[20] The chemistry of N,N-bis(trialkylsilyloxy)enamines 2.: Alkylation of primary amines with N,N-bis(trimethylsilyloxy)enamines [J].

Makarenkova, LM ;

Bliznets, IV ;

Ioffe, SL ;

Strelenko, YA ;

Tartakovsky, VA .

RUSSIAN CHEMICAL BULLETIN, 2000, 49 (07) :1261-1269

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