LITHIUM PERCHLORATE-ASSISTED SUBSTITUTION-REACTIONS OF ALLYLIC ACETATES AND ALLYLIC ALCOHOLS

被引：45

作者：

PEARSON, WH

SCHKERYANTZ, JM

机构：

[1] Department of Chemistry, Willard H. Dow Laboratories, University of Michigan, Ann Arbor

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1992年 / 57卷 / 11期

关键词：

D O I：

10.1021/jo00037a004

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Substitution reactions of allylic acetates and allylic alcohols by a variety of nucleophiles proceed smoothly in the presence of lithium perchlorate in ether, providing a convenient alternative to transition metal catalyzed methods.

引用

页码：2986 / 2987

页数：2

共 19 条

[1] THE REGIOSELECTIVITIES AND STEREOSELECTIVITIES OF THE REACTION OF ALLYL ACETATES AND SILYL KETENE ACETALS CATALYZED BY PD(0) COMPLEXES - A NEW ROUTE TO CYCLOPROPANE DERIVATIVES [J].

CARFAGNA, C ;

MARIANI, L ;

MUSCO, A ;

SALLESE, G ;

SANTI, R .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (12) :3924-3927

[2] ON THE ADDITION OF ALLYLTRIMETHYLSILANE TO GLYCAL ACETATES [J].

DANISHEFSKY, S ;

KERWIN, JF .

JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (19) :3803-3805

[3] ALPHA-C-GLYCOPYRANOSIDES FROM LEWIS ACID-CATALYZED CONDENSATIONS OF ACETYLATED GLYCALS AND ENOL SILANES [J].

DAWE, RD ;

FRASERREID, B .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1981, (22) :1180-1181

[4] SOME USES OF SILICON-COMPOUNDS IN ORGANIC-SYNTHESIS [J].

FLEMING, I .

CHEMICAL SOCIETY REVIEWS, 1981, 10 (01) :83-111

[5]

GODLESKI SA, COMPREHENSIVE ORGANI

[6]

Grieco P.A., 1991, ALDRICHIM ACTA, V24, P59

[7] [1,3] SIGMATROPIC REARRANGEMENT OF ALLYL VINYL ETHERS AT AMBIENT-TEMPERATURE IN 3.0M LITHIUM PERCHLORATE-DIETHYL ETHER [J].

GRIECO, PA ;

CLARK, JD ;

JAGOE, CT .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (14) :5488-5489

[8] A MILD METHOD FOR THE SYNTHESIS OF ANOMERICALLY ALLYLATED C-GLYCOPYRANOSIDES AND C-GLYCOFURANOSIDES [J].

KOZIKOWSKI, AP ;

SORGI, KL .

TETRAHEDRON LETTERS, 1982, 23 (22) :2281-2284

[9] A HIGHLY REGIOSELECTIVE REACTION OF ALLYLIC ACETATES WITH SILYLATED CARBON NUCLEOPHILES DIRECTED BY A SULFENYL GROUP [J].

KUDO, K ;

SAIGO, K ;

HASHIMOTO, Y ;

HOUCHIGAI, H ;

HASEGAWA, M .

TETRAHEDRON LETTERS, 1991, 32 (34) :4311-4312

[10] NEW SYNTHETIC METHODS FOR ALPHA, BETA-UNSATURATED KETONES, ALDEHYDES, ESTERS AND LACTONES BY THE PALLADIUM-CATALYZED REACTIONS OF SILYL ENOL ETHERS, KETENE SILYL ACETALS, AND ENOL ACETATES WITH ALLYL CARBONATES [J].

MINAMI, I ;

TAKAHASHI, K ;

SHIMIZU, I ;

KIMURA, T ;

TSUJI, J .

TETRAHEDRON, 1986, 42 (11) :2971-2977

← 1 2 →