Efficient preparation of vinylcyclopropane by S-N' cyclization of the organolithium derived from (E)-5-iodo-1-methoxy-2-pentene

被引：18

作者：

Bailey, WF

Tao, Y

机构：

[1] Department of Chemistry, University of Connecticut, Storrs

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 35期

关键词：

D O I：

10.1016/S0040-4039(97)01423-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

(5-Methoxy-E-3-pentenyl)lithium (1), which may be prepared in virtually quantitative yield from the corresponding iodide by low-temperature lithium-iodine exchange, cyclizes with expulsion of the allylic methoxy on warming in the presence of TMEDA to afford vinylcyclopropane in 88 % yield. (C) 1997 Elsevier Science Ltd.

引用

页码：6157 / 6158

页数：2

共 16 条

[1] SYNTHESIS OF A DITHIA-18-CROWN-6-TETRACARBOXYLIC ACID
ANANTANARAYAN, A
DUTTON, PJ
FYLES, TM
PITRE, MJ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (05) : 752 - 755
[2] ARORA S, 1973, SYNTHESIS-STUTTGART, P146
[3] Bailey W. F., 1994, ADV DETAILED REACTIO, V3, P251
[4] CONVENIENT GENERAL-METHOD FOR THE PREPARATION OF PRIMARY ALKYLLITHIUMS BY LITHIUM IODINE EXCHANGE
BAILEY, WF
PUNZALAN, ER
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (19) : 5404 - 5406
[5] ANIONIC CYCLIZATIONS OF ALPHA-ALKOXY LITHIUMS - NEW, STEREOSELECTIVE ROUTES TO SUBSTITUTED TETRAHYDROFURANS
BROKA, CA
LEE, WJ
SHEN, T
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (06) : 1336 - 1338
[6] VINYLLITHIUM CYCLIZATIONS WITH UNACTIVATED ALKENES AS INTERNAL ELECTROPHILES - STEREOSELECTIVE FORMATION OF SUBSTITUTED METHYLENECYCLOPENTANES
CHAMBERLIN, AR
BLOOM, SH
CERVINI, LA
FOTSCH, CH
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (14) : 4788 - 4796
[7] DEMJANOW NJ, 1922, CHEM BER, V55, P2718
[8] METALATED ALLYLIC ETHERS AS HOMOENOLATE ANION EQUIVALENTS
EVANS, DA
ANDREWS, GC
BUCKWALT.B
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (17) : 5560 - 5561
[9] FORMATION OF CYCLIZED, INCLUDING 3,5-CYCLOSTEROID, ALKENES FROM BETA,GAMMA-UNSATURATED GRIGNARD-REAGENTS INDUCED BY ELIMINATION OF A DELTA-ALKOXY GROUP
FISCHER, PM
HOWDEN, MEH
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1987, (03): : 475 - 479
[10] RING FORMATION THROUGH INTRAMOLECULAR SN' DISPLACEMENT OF AN ALLYLIC METHOXY SUBSTITUENT
HARMS, AE
STILLE, JR
TAYLOR, SK
[J]. ORGANOMETALLICS, 1994, 13 (04) : 1456 - 1464

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