Catalytic asymmetric iodocarbocyclization reaction

被引:40
作者
Inoue, T
Kitagawa, O
Ochiai, O
Shiro, M
Taguchi, T
机构
[1] TOKYO COLL PHARM,HACHIOJI,TOKYO 19203,JAPAN
[2] RIGAKU CORP,AKISHIMA,TOKYO 196,JAPAN
关键词
D O I
10.1016/0040-4039(95)02021-G
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The iodocarbocyclization reactions of 4-pentenylmalonate derivatives using 20 mol% of the chiral titamium complex in the presence of 12 and 2,6-dimethoxypyridine proceeded with high enantioselectivity to give good yields of cyclopentane cyclopentone derivatives. The origin of enantioselectivity in the present reaction is discussed on the basis of X-ray crystal structural data of the chiral titanium complex from acetylacetone, chiral diol and Ti(IV).
引用
收藏
页码:9333 / 9336
页数:4
相关论文
共 21 条
[1]   EVIDENCE FOR THE IMPORTANCE OF PI-PI-ATTRACTIVE INTERACTIONS IN ENANTIOSELECTIVE DIELS-ALDER REACTIONS CHIRAL CATALYSTS OF TYPE (RO)2TICL2 [J].
COREY, EJ ;
MATSUMURA, Y .
TETRAHEDRON LETTERS, 1991, 32 (44) :6289-6292
[2]  
GOATHELF KV, 1995, J AM CHEM SOC, V117, P4435
[3]   ENANTIOSELECTIVE IODOCARBOCYCLIZATION OF 4-ALKENYLMALONATE DERIVATIVES USING A CHIRAL TITANIUM COMPLEX [J].
INOUE, T ;
KITAGAWA, O ;
KURUMIZAWA, S ;
OCHIAI, O ;
TAGUCHI, T .
TETRAHEDRON LETTERS, 1995, 36 (09) :1479-1482
[4]   DIASTEREOSELECTIVE IODOCARBOCYCLIZATION REACTION OF 8-PHENYLMENTHYL ALLYLMALONATE - AN EFFICIENT PREPARATION OF A SYNTHETIC INTERMEDIATE OF CYCLOPROPANE AMINO-ACIDS [J].
INOUE, T ;
KITAGAWA, O ;
OCHIAI, O ;
TAGUCHI, T .
TETRAHEDRON-ASYMMETRY, 1995, 6 (03) :691-692
[5]   IONIC IODOCARBOCYCLIZATION REACTION [J].
KITAGAWA, O ;
INOUE, T ;
TAGUCHI, T .
TETRAHEDRON LETTERS, 1992, 33 (16) :2167-2170
[6]   IONIC IODOCARBOCYCLIZATION REACTIONS OF 4-ALKENYLMALONATE AND 4-ALKYNYLMALONATE DERIVATIVES [J].
KITAGAWA, O ;
INOUE, T ;
HIRANO, K ;
TAGUCHI, T .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (11) :3106-3112
[7]   DIASTEREOSELECTIVE IODOCARBOCYCLIZATION OF 4-PENTENYLMALONATE DERIVATIVES - APPLICATION TO CYCLOSARKOMYCIN SYNTHESIS [J].
KITAGAWA, O ;
INOUE, T ;
TAGUCHI, T .
TETRAHEDRON LETTERS, 1994, 35 (07) :1059-1062
[8]   HOMOALLYLIC CHIRAL INDUCTION IN THE SYNTHESIS OF 2,4-DISUBSTITUTED TETRAHYDROFURANS BY IODOETHERIFICATION - SYNTHETIC SCOPE AND CHIRAL INDUCTION MECHANISM [J].
LABELLE, M ;
MORTON, HE ;
GUINDON, Y ;
SPRINGER, JP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (14) :4533-4540
[9]  
MIKAMI K, 1992, SYNLETT, P255
[10]  
MORISON JD, 1991, ASYMMETRIC SYNTHESIS, V5, P1