ZNBR2-CATALYZED STEREOSPECIFIC 1,4-ELIMINATION OF 1-METHOXYMETHYL-2-(TRIMETHYLSILYLMETHYL)-CYCLOBUTANES - STEREOSELECTIVE PREPARATION OF 1,1,5-TRISUBSTITUTED (E)-DIENES AND (Z)-1,5-DIENES

被引：11

作者：

FUJIWARA, T ^{[1
]}

SUDA, A ^{[1
]}

TAKEDA, T ^{[1
]}

机构：

[1] TOKYO UNIV AGR & TECHNOL, DEPT APPL CHEM, KOGANEI, TOKYO 184, JAPAN

来源：

CHEMISTRY LETTERS | 1992年 / 09期

关键词：

D O I：

10.1246/cl.1992.1631

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The stereoselective addition of alkylmetals to 2-(trimethylsilylmethyl)-1-cyclobutyl ketones and the ZnBr2-catalyzed stereospecific ring-opening reaction of resulting 1-methoxymethyl-2-(trimethylsilylmethyl)cyclobutanes gave 1,1,5-trisubstituted 1,5-dienes with high stereoselectivity.

引用

页码：1631 / 1634

页数：4

共 12 条

[1] A SYNTHETIC EQUIVALENT FOR THE BUTADIENYL CARBONIUM-ION - USE OF 4-(TRIMETHYLSILYL)BUT-2-YNAL FOR PREPARATION OF 1,3-DIENES AND MACROEXPANSION OF CYCLIC-KETONES
ANGOH, AG
CLIVE, DLJ
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1984, (08) : 534 - 536
[2] TOTAL SYNTHESIS OF D,L-CARYOPHYLLENE + D,L-ISOCARYOPHYLLENE
COREY, EJ
MITRA, RB
UDA, H
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1964, 86 (03) : 485 - &
[3] A NEW STEREOSPECIFIC SYNTHESIS OF TRISUBSTITUTED OLEFINS . STEREOSPECIFIC SYNTHESIS OF FARNESOL
COREY, EJ
KATZENEL.JA
POSNER, GH
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (16) : 4245 - &
[4] TELLUROLATE-INDUCED 1,4-ELIMINATION OF 1,4-DIBROMO 2-ENES - SYNTHESES OF 1,3-DIENES
ENGMAN, L
BYSTROM, SE
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (17) : 3170 - 3174
[5] TRIETHYLALUMINUM CATALYZED RING-OPENING REACTION OF 1-ACETYL-2-[(TRIMETHYLSILYL)-METHYL]CYCLOBUTANES - STEREOSELECTIVE PREPARATION OF (Z)-ENOL TRIMETHYLSILYL ETHERS
FUJIWARA, T
SUDA, A
TAKEDA, T
[J]. CHEMISTRY LETTERS, 1991, (09) : 1619 - 1622
[6] MARSHALL JA, 1971, SYNTH-INT J METHODS, P229
[7] MARSHALL JA, 1970, TETRAHEDRON LETT, P3861
[8] MCDOUGAL PG, 1987, J ORG CHEM, V52, P4819
[9] SILICON-DIRECTED BECKMANN FRAGMENTATION - CATALYTIC CLEAVAGE OF CYCLIC BETA-TRIMETHYLSILYLKETOXIME ACETATES WITH TRIMETHYLSILYL TRIFLUOROMETHANESULFONATE
NISHIYAMA, H
SAKUTA, K
OSAKA, N
ITOH, K
[J]. TETRAHEDRON LETTERS, 1983, 24 (37) : 4021 - 4024
[10] STEREOCHEMISTRY OF AN OXIDATIVE 1,4-FRAGMENTATION OF GAMMA-STANNYL ALCOHOLS WITH A HYPERVALENT ORGANOIODINE COMPOUND AND THE SYNTHESIS OF ERYTHRO-6-ACETOXYHEXADECAN-5-OLIDE
OCHIAI, M
UKITA, T
NAGAO, Y
FUJITA, E
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1985, (10) : 637 - 638

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