SAMARIUM DIIODIDE MEDIATED ALKYLATION OF SATURATED HETEROCYCLES ALPHA TO NITROGEN

被引：23

作者：

BOOTH, SE ^{[1
]}

BENNECHE, T ^{[1
]}

UNDHEIM, K ^{[1
]}

机构：

[1] UNIV OSLO,DEPT CHEM,N-0315 OSLO,NORWAY

来源：

TETRAHEDRON | 1995年 / 51卷 / 12期

关键词：

D O I：

10.1016/0040-4020(95)00081-I

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A method for alpha-alkylation of saturated 5-, 6-, 7- and and 8-membered aza-heterocycles is described. The auxiliary is an o-iodobenzyl group attached at the nitrogen. A radical introduced in the o-position is transferred to the amine alpha-position which subsequently leads to an addition reaction with pentan-3-one.

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收藏

页码：3665 / 3674

页数：10

相关论文

共 23 条

[1] ALPHA-LITHIOAMINE SYNTHETIC EQUIVALENTS - SYNTHESES OF DIASTEREOISOMERS FROM THE BOC PIPERIDINES [J].

BEAK, P ;

LEE, WK .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (09) :2578-2580

[2] SYNTHESIS OF SPIRO-COMPOUNDS RELATED TO FREDERICAMYCIN-A [J].

BENNETT, SM ;

CLIVE, DLJ .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1986, (11) :878-880

[3]

BORTHWICK AD, 1990, TETRAHEDRON LETT, V31, P6811

[4] INTERNAL HYDROGEN ABSTRACTION BY ACTIVATED NEOCARZINOSTATIN - QUENCHING OF THE RADICAL AT C2 BY HYDROGEN-ATOM TRANSFER FROM THE ALPHA-CARBON OF THE ADDUCTED THIOL [J].

CHIN, DH ;

GOLDBERG, IH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (05) :1914-1915

[5]

CURRAN DP, 1990, SYNLETT, P773

[6] THE SAMARIUM GRIGNARD REACTION - INSITU FORMATION AND REACTIONS OF PRIMARY AND SECONDARY ALKYLSAMARIUM(III) REAGENTS [J].

CURRAN, DP ;

TOTLEBEN, MJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (15) :6050-6058

[7] TRANSLOCATION OF RADICAL SITES BY INTRAMOLECULAR 1,5-HYDROGEN ATOM TRANSFER [J].

CURRAN, DP ;

KIM, D ;

LIU, HT ;

SHEN, W .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (17) :5900-5902

[8] RADICAL TRANSLOCATION REACTIONS OF ORTHO-IODOANILIDES - THE USE OF CARBON HYDROGEN-BONDS AS PRECURSORS OF RADICALS ADJACENT TO CARBONYL GROUPS [J].

CURRAN, DP ;

ABRAHAM, AC ;

LIU, HT .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (14) :4335-4337

[9] A SAMARIUM(II) IODIDE PROMOTED TANDEM RADICAL CYCLIZATION - THE TOTAL SYNTHESIS OF (+/-)-HYPNOPHILIN AND THE FORMAL SYNTHESIS OF (+/-)-CORIOLIN [J].

FEVIG, TL ;

ELLIOTT, RL ;

CURRAN, DP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (15) :5064-5067

[10] DIVALENT LANTHANIDE DERIVATIVES IN ORGANIC-SYNTHESIS .1. MILD PREPARATION OF SMI2 AND YBI2 AND THEIR USE AS REDUCING OR COUPLING AGENTS [J].

GIRARD, P ;

NAMY, JL ;

KAGAN, HB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (08) :2693-2698