PALLADIUM-CATALYZED STEREOCONTROLLED ENDO CYCLIZATION OF 3-HYDROXYPROPYL-1,3-CYCLOHEXADIENE LEADING TO VERSATILE FUSED TETRAHYDROPYRANS

被引：0

作者：

KOROLEVA, EB ^{[1
]}

BACKVALL, JE ^{[1
]}

ANDERSSON, PG ^{[1
]}

机构：

[1] UNIV UPPSALA,DEPT ORGAN CHEM,S-75121 UPPSALA,SWEDEN

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 30期

关键词：

D O I：

10.1016/00404-0399(50)0989P-

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A palladium-catalyzed synthesis of stereodefined fused tetrahydropyrans from 2-substituted 1,3-cyclohexadienes is presented. The reaction takes place via an intramolecular 1,4-oxidation of the conjugated diene via a (pi-allyl)palladium intermediate. The stereochemical outcome of the reaction can be controlled to give either cis or trans 1,4-addition over the conjugated diene. The structure of the products was established by X-ray crystallography.

引用

页码：5397 / 5400

页数：4

共 9 条

[1] BACKVALL JE, 1990, J AM CHEM SOC, V112, P3683
[2] IMPROVED PALLADIUM-CATALYZED 1,4-HALOACYLOXYLATION AND 1,4-DIACYLOXYLATION OF CYCLIC CONJUGATED DIENES
BACKVALL, JE
GRANBERG, KL
HOPKINS, RB
[J]. ACTA CHEMICA SCANDINAVICA, 1990, 44 (05): : 492 - 499
[3] BACKVALL JE, 1991, J ORG CHEM, V56, P2274
[4] BACKVALL JE, 1992, J AM CHEM SOC, V114, P6374
[5] BACKVALL JE, 1985, J AM CHEM SOC, V107, P3676
[6] BACKVALL JE, 1984, J ORG CHEM, V49, P4619
[7] STEREOCONTROLLED LACTONIZATION REACTIONS VIA PALLADIUM-CATALYSIS
BACKVALL, JE
ANDERSSON, PG
VAGBERG, JO
[J]. TETRAHEDRON LETTERS, 1989, 30 (01) : 137 - 140
[8] BACKVALL JE, 1993, J ORG CHEM, V58, P5645
[9] HWU JR, 1992, TETRAHEDRON LETT, V43, P6469

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