LIBF4 - A MILD LEWIS ACID FOR INTRAMOLECULAR DIELS-ALDER REACTIONS

被引：44

作者：

SMITH, DA ^{[1
]}

HOUK, KN ^{[1
]}

机构：

[1] UNIV CALIF LOS ANGELES,DEPT CHEM & BIOCHEM,LOS ANGELES,CA 90024

来源：

TETRAHEDRON LETTERS | 1991年 / 32卷 / 12期

关键词：

D O I：

10.1016/S0040-4039(00)74269-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The lithium salts, LiClO4 and LiBF4, have been investigated for their potential use as Lewis acid catalysts in the intramolecular Diels-Alder reaction. No cycloaddition of the trienone, 1, is observed when LiClO4 is used. LiBF4 provides quantitative yield of the cis-fused cycloadduct in 72 hours at room temperature. The catalysis is ascribed to the slow release of BF3 rather than to the lithium cation.

引用

页码：1549 / 1552

页数：4

共 16 条

[1] Ciganek E., 1984, ORG REACT NY, V32, P1, DOI DOI 10.1002/0471264180.OR032.01
[2] DOYLE MP, 1975, TETRAHEDRON LETT, P4201
[3] 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
[4] BORON TRIFLUORIDE CO-ORDINATION COMPOUNDS
GREENWOOD, NN
MARTIN, RL
[J]. QUARTERLY REVIEWS, 1954, 8 (01): : 1 - 39
[5] DRAMATIC RATE ACCELERATIONS OF DIELS-ALDER REACTIONS IN 5-M LITHIUM PERCHLORATE DIETHYL-ETHER - THE CANTHARIDIN PROBLEM REEXAMINED
GRIECO, PA
NUNES, JJ
GAUL, MD
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (11) : 4595 - 4596
[6] CHEMISTRY OF BETA-TRIMETHYLSILYLETHANOL .2. A NEW METHOD FOR PROTECTION OF AN ANOMERIC CENTER IN PYRANOSIDES
LIPSHUTZ, BH
PEGRAM, JJ
MOREY, MC
[J]. TETRAHEDRON LETTERS, 1981, 22 (46) : 4603 - 4606
[7] HYDROLYSIS OF ACETALS AND KETALS USING LIBF4
LIPSHUTZ, BH
HARVEY, DF
[J]. SYNTHETIC COMMUNICATIONS, 1982, 12 (04) : 267 - 277
[8] CLEAVAGE OF TERT-BUTYLDIMETHYLSILYL ETHERS BY TETRAFLUOROBORATE SALTS
METCALF, BW
BURKHART, JP
JUND, K
[J]. TETRAHEDRON LETTERS, 1980, 21 (01) : 35 - 36
[9] DIMETHYL SULFOXIDE-TRIFLUOROACETIC ANHYDRIDE - NEW REAGENT FOR OXIDATION OF ALCOHOLS TO CARBONYLS
OMURA, K
SHARMA, AK
SWERN, D
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (06) : 957 - 962
[10] STEREOCHEMICAL ASPECTS OF THE INTRAMOLECULAR DIELS-ALDER REACTIONS OF DECA-2,7,9-TRIENOATE ESTERS .3. THERMAL, LEWIS ACID-CATALYZED, AND ASYMMETRIC CYCLIZATIONS
ROUSH, WR
GILLIS, HR
KO, AI
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (08) : 2269 - 2283

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