Intramolecular cationic cyclizations initiated by electrocyclic cleavage of cyclopropanes. Synthesis of trienic cyclopentane derivatives

被引：12

作者：

Gassman, PG

Tan, LS

Hoye, TR

机构：

[1] Department of Chemistry, University of Minnesota, Minneapolis

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 04期

关键词：

D O I：

10.1016/0040-4039(95)02213-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The electrocyclic opening of dibromocyclopropane derivatives containing a tethered diene unit provides a good route to trienic cyclopentane derivatives. In one instance a bicyclic product arising from a formal 4 + 2 cycloaddition process was observed.

引用

页码：439 / 442

页数：4

共 11 条

[1] A STEREOSELECTIVE TOTAL SYNTHESIS OF (+/-)-GAMMA-LYCORANE
BANWELL, MG
WU, AW
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (19): : 2671 - 2672
[2] CATIONIC CYCLIZATIONS INITIATED BY ELECTROCYCLIC CLEAVAGE OF CYCLOPROPANES - SYNTHESIS OF LACTONES, TETRAHYDROPYRANS, AND TETRAHYDROFURANS
DANHEISER, RL
MORIN, JM
YU, M
BASAK, A
[J]. TETRAHEDRON LETTERS, 1981, 22 (42) : 4205 - 4208
[3] INTRAMOLECULAR CYCLIZATION OF AN ALLYL CATION - THE FORMATION OF 11-MEMBERED CARBOCYCLIC RINGS VIA CATIONIC PROCESSES
GASSMAN, PG
RIEHLE, RJ
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (06) : 2319 - 2320
[4] CONTROL OF REGIOSPECIFICITY IN IONIC DIELS-ALDER REACTIONS - THE USE OF ALLYLIC ALCOHOLS AND ALLYLIC ETHERS AS PRECURSORS OF DIENOPHILIC ALLYL CATIONS
GASSMAN, PG
SINGLETON, DA
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (15) : 3075 - 3076
[5] THE LOW-TEMPERATURE, IONIC DIELS-ALDER ADDITION OF VINYL ORTHO ESTERS TO 1,3-DIENES
GASSMAN, PG
CHAVAN, SP
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (10) : 2392 - 2394
[6] ACROLEIN ACETALS AS ALLYL CATION PRECURSORS IN THE IONIC DIELS-ALDER REACTION
GASSMAN, PG
SINGLETON, DA
WILWERDING, JJ
CHAVAN, SP
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (07) : 2182 - 2184
[7] ACID-CATALYZED INTRAMOLECULAR DIELS-ALDER REACTIONS - THE CYCLOADDITION OF ALLYL CATIONS TO 1,3-DIENES
GASSMAN, PG
SINGLETON, DA
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (20) : 6085 - 6086
[8] INFLUENCE OF ALKYL SUBSTITUTION ON THE INTRAMOLECULAR IONIC DIELS-ALDER REACTION OF TETRAENES
GORMAN, DB
GASSMAN, PG
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (04) : 977 - 985
[9] STUDIES ON HETEROCAGE COMPOUNDS .5. REACTION OF 5-HYDROXYMETHYL-2-NORBORNENE WITH DIHALOCARBENE - NOVEL SYNTHESIS OF SOME OXA-MODIFIED ADAMANTANE ANALOGS
SASAKI, T
EGUCHI, S
KIRIYAMA, T
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (12) : 2230 - 2234
[10] SCHREIBER SL, ORG SYNTH COLL, V7, P168

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