STEREOSELECTIVE REDUCTION OF SOME INDOLES WITH TRIETHYLSILANE-TRIFLUOROACETIC ACID

被引：70

作者：

LANZILOTTI, AE ^{[1
]}

LITTELL, R ^{[1
]}

FANSHAWE, WJ ^{[1
]}

MCKENZIE, TC ^{[1
]}

LOVELL, FM ^{[1
]}

机构：

[1] AMER CYANAMID CO,LEDERLE LABS,DIV MED RES,PEARL RIVER,NY 10965

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1979年 / 44卷 / 26期

关键词：

D O I：

10.1021/jo00394a013

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The completely stereoselective reduction of indoles to cis-indolines by triethylsilane-trifluoroacetic acid is demonstrated. A rationalization of this stereoselectivity is offered. The precursor indoles were prepared by the Fisher indole condensation with levulinic acid (7). 3, 4-Dimethoxyhydrazine (6a) gave only the 5, 6-dimethoxyindole 8a while 3, 4-dichlorohydrazine (6d) gave a 1:1 mixture of the isomeric chloroindoles 8d and 8e which were separated by preparative liquid chromatography. © 1979, American Chemical Society. All rights reserved.

引用

页码：4809 / 4813

页数：5

共 31 条

[11] ON APPLICATION OF PHASE RELATIONSHIPS TO COMPLEX STRUCTURES .2. GETTING A GOOD START [J].

GERMAIN, G ;

MAIN, P ;

WOOLFSON, MM .

ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL CRYSTALLOGRAPHY AND CRYSTAL CHEMISTRY, 1970, B 26 :274-&

[12]

GRIBBLE GW, 1974, J AM CHEM SOC, V96, P7814

[13] A CORRELATION OF REACTION RATES [J].

HAMMOND, GS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1955, 77 (02) :334-338

[14] PROTONATION OF INDOLES - POSITION OF PROTONATION [J].

HINMAN, RL ;

WHIPPLE, EB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1962, 84 (13) :2534-&

[15]

KIKUGAWA Y, 1978, SYNTHESIS-STUTTGART, P447

[16]

KURSANOV DN, 1974, SYNTHESIS-STUTTGART, P633

[17]

LANZILOTTI AE, J LABELLED COMPD

[18] BORANE COMPLEXES IN TRIFLUOROACETIC-ACID - REDUCTION OF INDOLES TO INDOLINES AND GENERATION OF BIS(TRIFLUOROACETOXY)BORANE [J].

MARYANOFF, BE ;

MCCOMSEY, DF .

JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (13) :2733-2734

[19] REACTION OF INDOLES WITH DIBORANE [J].

MONTI, SA ;

SCHMIDT, RR .

TETRAHEDRON, 1971, 27 (15) :3331-+

[20]

PARNES ZN, 1972, J ORG CHEM USSR, V8, P2613

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