PREPARATION OF OPTICALLY-ACTIVE (R)-ALLENE-1,3-DICARBOXYLATES AND (S)-ALLENE-1,3-DICARBOXYLATES AND THEIR ASYMMETRIC CYCLOADDITION REACTIONS WITH CYCLOPENTADIENE

被引：24

作者：

ASO, M

IKEDA, I

KAWABE, T

SHIRO, M

KANEMATSU, K

机构：

[1] KYUSHU UNIV 62,FAC PHARMACEUT SCI,INST SYNTHET ORGAN CHEM,HIGASHI KU,MAIDASHI,FUKUOKA 812,JAPAN

[2] RIGAKU CORP,AKISHIMA,TOKYO 196,JAPAN

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 39期

关键词：

OPTICALLY ACTIVE ALLENE-1,3-DICARBOXYLATE; ASYMMETRIC DIELS-ALDER REACTION;

D O I：

10.1016/0040-4039(92)89032-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Optically active (R)- and (S)-allene- 1,3-dicarboxylates were prepared, and their asymmetric Diels-Alder reactions with cyclopentadiene in the presence of Lewis acid proceeded to afford the endo-adducts in high yields. The absolute configuration of the adduct was completely confirmed by X-ray analysis.

引用

页码：5787 / 5790

页数：4

共 7 条

[1] ABSOLUTE CONFIGURATION OF PENTADIENDIOIC ACID
AGOSTA, WC
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1964, 86 (13) : 2638 - &
[2] INTER-MOLECULAR AND INTRA-MOLECULAR REACTIONS OF ALLENE-1,3-DICARBOXYLIC ACID-ESTERS WITH 2-VINYLFURANS AND 2-VINYLTHIOPHENES - A POTENTIAL ROUTE TO A BC RING PRECURSOR OF THE NAGILACTONES
DELL, CP
SMITH, EH
WARBURTON, D
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1985, (04): : 747 - 756
[3] ASYMMETRIC DIELS-ALDER REACTION - COOPERATIVE BLOCKING EFFECT IN ORGANIC-SYNTHESIS
FURUTA, K
IWANAGA, K
YAMAMOTO, H
[J]. TETRAHEDRON LETTERS, 1986, 27 (37) : 4507 - 4510
[4] SYNTHESES OF (+/-)- AND (-)-CIS-TRIKENTRIN-A, (+/-)- AND (-)-TRANS-TRIKENTRIN-A, (+/-)-CIS-TRIKENTRIN-B, (+/-)-TRANS-TRIKENTRIN-B, AND (+/-)-ISO-TRANS-TRIKENTRIN-B
MURATAKE, H
WATANABE, M
GOTO, K
NATSUME, M
[J]. TETRAHEDRON, 1990, 46 (12) : 4179 - 4192
[5] ASYMMETRIC DIELS-ALDER REACTION OF A CHIRAL ALLENIC ESTER - ENANTIOSELECTIVE SYNTHESIS OF (-)-BETA-SANTALENE
OPPOLZER, W
CHAPUIS, C
[J]. TETRAHEDRON LETTERS, 1983, 24 (43) : 4665 - 4668
[6] THE TOTAL SYNTHESIS OF (+)-CIS-TRIKENTRIN-B VIA ALLENE INTRAMOLECULAR CYCLO-ADDITION
YASUKOUCHI, T
KANEMATSU, K
[J]. TETRAHEDRON LETTERS, 1989, 30 (47) : 6559 - 6562
[7] PERISELECTIVE INTRAMOLECULAR CYCLO-ADDITION OF ALLENE-1,3-DICARBOXYLATES - UNUSUAL STRUCTURAL FEATURE OF [2 + 2] CYCLOADDUCTS
YOSHIDA, M
HIDAKA, Y
NAWATA, Y
RUDZINSKI, JM
OSAWA, E
KANEMATSU, K
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (04) : 1232 - 1238

← 1 →