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
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
收藏
页码:5787 / 5790
页数:4
相关论文
共 7 条
[1]   ABSOLUTE CONFIGURATION OF PENTADIENDIOIC ACID [J].
AGOSTA, WC .
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 [J].
DELL, CP ;
SMITH, EH ;
WARBURTON, D .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1985, (04) :747-756
[3]   ASYMMETRIC DIELS-ALDER REACTION - COOPERATIVE BLOCKING EFFECT IN ORGANIC-SYNTHESIS [J].
FURUTA, K ;
IWANAGA, K ;
YAMAMOTO, H .
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 [J].
MURATAKE, H ;
WATANABE, M ;
GOTO, K ;
NATSUME, M .
TETRAHEDRON, 1990, 46 (12) :4179-4192
[5]   ASYMMETRIC DIELS-ALDER REACTION OF A CHIRAL ALLENIC ESTER - ENANTIOSELECTIVE SYNTHESIS OF (-)-BETA-SANTALENE [J].
OPPOLZER, W ;
CHAPUIS, C .
TETRAHEDRON LETTERS, 1983, 24 (43) :4665-4668
[6]   THE TOTAL SYNTHESIS OF (+)-CIS-TRIKENTRIN-B VIA ALLENE INTRAMOLECULAR CYCLO-ADDITION [J].
YASUKOUCHI, T ;
KANEMATSU, K .
TETRAHEDRON LETTERS, 1989, 30 (47) :6559-6562
[7]   PERISELECTIVE INTRAMOLECULAR CYCLO-ADDITION OF ALLENE-1,3-DICARBOXYLATES - UNUSUAL STRUCTURAL FEATURE OF [2 + 2] CYCLOADDUCTS [J].
YOSHIDA, M ;
HIDAKA, Y ;
NAWATA, Y ;
RUDZINSKI, JM ;
OSAWA, E ;
KANEMATSU, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (04) :1232-1238