DIASTEREOFACIAL SELECTIVITY IN DIELS-ALDER REACTIONS OF BUTA-1,3-DIENES HAVING STEREOGENIC ALLYLIC HETEROATOM SUBSTITUENTS AT THE C-2 POSITION

被引：27

作者：

HATAKEYAMA, S ^{[1
]}

SUGAWARA, K ^{[1
]}

TAKANO, S ^{[1
]}

机构：

[1] TOHOKU UNIV,INST PHARMACEUT,SENDAI,MIYAGI 980,JAPAN

来源：

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS | 1992年 / 13期

关键词：

D O I：

10.1039/c39920000953

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Diels-Alder reactions of ten 2-substituted buta-1,3-dienes 1a-j with N-phenylmaleimide were examined under various conditions, demonstrating that an allylic heteroatom substituent at the C-2 position exerts significant directing effect on diastereofacial selection and also that the diastereofacial selectivity can be enhanced by use of 5 mol dm-3 LiClO4-Et2O as a reaction medium.

引用

页码：953 / 955

页数：3

共 17 条

[1] THE POLARITY OF SOLUTIONS OF LITHIUM PERCHLORATE IN WATERFREE ETHERS
BRAUN, R
SAUER, J
[J]. CHEMISCHE BERICHTE-RECUEIL, 1986, 119 (04): : 1269 - 1274
[2] SILICON-DIRECTED DIENE SYNTHESIS
BROWN, PA
BONNERT, RV
JENKINS, PR
LAWRENCE, NJ
SELIM, MR
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (08): : 1893 - 1900
[3] EFFECT OF ALLYLIC SUBSTITUENTS ON THE FACE SELECTIVITY OF DIELS-ALDER REACTIONS OF SEMICYCLIC DIENES
DATTA, SC
FRANCK, RW
TRIPATHY, R
QUIGLEY, GJ
HUANG, L
CHEN, S
SIHAED, A
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (23) : 8472 - 8478
[4] FACE SELECTIVITY IN DIELS-ALDER REACTIONS OF CHIRAL DIENES CONTAINING ALLYLIC SUBSTITUENTS
FISHER, MJ
HEHRE, WJ
KAHN, SD
OVERMAN, LE
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (14) : 4625 - 4633
[5] DIELS-ALDER REACTIONS OF DIENO-PYRANOSIDES - ANOMERIC VS ALLYLIC STEREOSELECTION
GIULIANO, RM
BUZBY, JH
MARCOPULOS, N
SPRINGER, JP
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (11) : 3555 - 3562
[6] Grieco P.A., 1991, ALDRICHIM ACTA, V24, P59
[7] 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
[8] ENANTIOCONTROLLED AND STEREOCONTROLLED SYNTHESES OF BRANCHED-CHAIN SUGAR, L-ARCANOSE AND L-OLIVOMYCOSE BASED ON THE CHEMISTRY OF 1-TRIMETHYLSILYL-2,3-BUTADIENE
HATAKEYAMA, S
SUGAWARA, K
TAKANO, S
[J]. TETRAHEDRON LETTERS, 1991, 32 (35) : 4513 - 4516
[9] PREPARATION OF RACEMIC AND CHIRAL ALKYL(1,3-BUTADIEN-2-YL)METHANOL DERIVATIVES UTILIZING 1-TRIMETHYLSILYL-2,3-BUTADIENE AS A DIENE SOURCE
HATAKEYAMA, S
SUGAWARA, K
KAWAMURA, M
TAKANO, S
[J]. TETRAHEDRON LETTERS, 1991, 32 (35) : 4509 - 4512
[10] CONCISE ENANTIOSELECTIVE SYNTHESIS OF A KEY SYNTHETIC INTERMEDIATE FOR ANTICANCER ANTHRACYCLINES BASED ON THE CHEMISTRY OF 1-TRIMETHYLSILYLBUTA-2,3-DIENE
HATAKEYAMA, S
SUGAWARA, K
TAKANO, S
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (21) : 1533 - 1534

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