CHEMICALLY LABILE STANNYLENE-NITROGEN BONDS - THE CHEMOSELECTIVE AND STEREOSELECTIVE SYNTHESIS OF N,N-BIS(TRIMETHYLSILYL)ENAMINES AND N,N-DIALKYLENAMINES

被引：12

作者：

BURNELLCURTY, C ^{[1
]}

ROSKAMP, EJ ^{[1
]}

机构：

[1] NORTHWESTERN UNIV,DEPT CHEM,EVANSTON,IL 60208

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1992年 / 57卷 / 19期

关键词：

D O I：

10.1021/jo00045a009

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The chemoselective reaction of Sn[N(TMS)2]2 with primary aldehydes leads to the stereoselective synthesis of trans-N,N-bis(trimethylsilyl)enamines. More reactive Sn(NR2)2 (R = Et, iPr, or piperidine) can be generated in situ and then treated with aldehydes or ketones to give trans enamines.

引用

收藏

页码：5063 / 5064

页数：2

相关论文

共 41 条

[31] ENAMINES OF ACYLSILANES - AN EASY ACCESS FROM ALPHA-SILOXY NITRILES [J].

PICARD, JP ;

AZIZELYUSUFI, A ;

CALAS, R ;

DUNOGUES, J ;

DUFFAUT, N .

ORGANOMETALLICS, 1984, 3 (11) :1660-1665

[32] AN IMPROVED PREPARATION OF ENAMINES OF ACYLSILANES, A NEW SYNTHESIS OF ACYLSILANES [J].

PICARD, JP ;

AIZPURUA, JM ;

ELYUSUFI, A ;

KOWALSKI, P .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1990, 391 (01) :13-18

[33] CARBONYL METHYLENATION USING A TITANIUM-ALUMINUM (TEBBE) COMPLEX [J].

PINE, SH ;

PETTIT, RJ ;

GEIB, GD ;

CRUZ, SG ;

GALLEGO, CH ;

TIJERINA, T ;

PINE, RD .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (08) :1212-1216

[34] RETRODIENE REACTIONS .9. SYNTHESIS BY FLASH THERMOLYSIS AND STUDY OF UNSTABLE PRIMARY ENAMINES [J].

RIPOLL, JL ;

LEBRUN, H ;

THUILLIER, A .

TETRAHEDRON, 1980, 36 (17) :2497-2503

[35] TIN(II) ORGANOSILYLAMINES [J].

SCHAEFFE.CD ;

ZUCKERMA.JJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (22) :7160-7162

[36] PREPARATION, ANALYSIS, AND REACTIVITY OF BIS[N,N-BIS(TRIMETHYLSILYL)AMINO]TIN(II) - AN ADVANCED UNDERGRADUATE LABORATORY PROJECT IN ORGANOMETALLIC SYNTHESIS [J].

SCHAEFFER, CD ;

MYERS, LK ;

COLEY, SM ;

OTTER, JC ;

YODER, CH .

JOURNAL OF CHEMICAL EDUCATION, 1990, 67 (04) :347-349

[37] A NEW SYNTHESIS OF 2-ALKYL AND 2-ACYL KETONES [J].

STORK, G ;

TERRELL, R ;

SZMUSZKOVICZ, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1954, 76 (07) :2029-2030

[38]

TAGUCHI K, 1971, J ORG CHEM, V36, P1570

[39] METAL-ASSISTED TERPENOID SYNTHESIS .7. HIGHLY ENANTIOSELECTIVE ISOMERIZATION OF PROCHIRAL ALLYLAMINES CATALYZED BY CHIRAL DIPHOSPHINE RHODIUM(I) COMPLEXES - PREPARATION OF OPTICALLY-ACTIVE ENAMINES [J].

TANI, K ;

YAMAGATA, T ;

AKUTAGAWA, S ;

KUMOBAYASHI, H ;

TAKETOMI, T ;

TAKAYA, H ;

MIYASHITA, A ;

NOYORI, R ;

OTSUKA, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (18) :5208-5217

[40] N,N-BIS(TRIMETHYLSILYL)ENAMINES-STEREOSELECTIVE SYNTHESIS FROM N,N-BIS(TRIMETHYLSILYL)THIOFORMAMIDE [J].

WALTER, W ;

LUKE, HW .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1977, 16 (08) :535-536

← 1 2 3 4 5 →