Catalytic asymmetric iodocarbocyclization reaction of 4-alkenylmalonates and its application to enantiotopic group selective reaction

被引：56

作者：

Inoue, T ^{[1
]}

Kitagawa, O ^{[1
]}

Saito, A ^{[1
]}

Taguchi, T ^{[1
]}

机构：

[1] TOKYO UNIV PHARM & LIFE SCI,HACHIOJI,TOKYO 19203,JAPAN

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1997年 / 62卷 / 21期

关键词：

D O I：

10.1021/jo970970d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The iodocarbocyclization reaction of 4-alkenylmalonate derivatives proceeded with excellent enantioselectivity (greater than or equal to 95% ee) in the presence of 10-40 mol % of Ti(TADDOLate)(2). The Ti(TADDOLate)(2)-mediated catalytic asymmetric reaction was extended to the enantiotopic group selective reaction of bisalkenylated malonates, giving rise to trisubstituted cyclopentanoid compounds with both high diastereoselectivity (86-94% de) and excellent enantioselectivity (greater than or equal to 95% ee). An efficient synthesis of (+)-boschnialactone from the product of the present reaction was also achieved.

引用

页码：7384 / 7389

页数：6

共 39 条

[1] [Anonymous], ASYMMETRIC SYNTHESIS
[2] NOVEL ROUTE TO SOME BIOLOGICALLY IMPORTANT COMPOUNDS STARTING WITH A COMMON CHIRAL, BICYCLIC, FUSED LACTONE - ENANTIOSELECTIVE SYNTHESIS OF (-)-BOSCHNIALACTONE AND 2 ANTITHROMBOTICS
ARAI, Y
KAWANAMI, S
KOIZUMI, T
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (12): : 2969 - 2975
[3] ENANTIOSELECTIVE SYNTHESIS OF (-)-BOSCHNIALACTONE
ARAI, Y
KAWANAMI, S
KOIZUMI, T
[J]. CHEMISTRY LETTERS, 1990, (09) : 1585 - 1586
[4] Bartlett P.A., 1984, ASYMMETRIC SYNTHESIS, V3, P411
[5] THE IODINATION AND IODOCYCLISATION OF SOME ALKENYLMALONATES
BECKWITH, ALJ
TOZER, MJ
[J]. TETRAHEDRON LETTERS, 1992, 33 (34) : 4975 - 4978
[6] Bougault M. J., 1904, CR HEBD ACAD SCI, V139, P864
[7] A ONE-STEP SYNTHESIS OF FUNCTIONALIZED LACTAMS AND SPIROLACTAMS FROM UNSATURATED BETA-KETOAMIDES
COSSY, J
THELLEND, A
[J]. TETRAHEDRON LETTERS, 1990, 31 (10) : 1427 - 1428
[8] DAHINDEN R, 1995, ENCY REAGENTS ORGANI, V3, P2167
[9] GARDILLO G, 1990, TETRAHEDRON, V46, P3321
[10] Catalytic asymmetric iodocarbocyclization reaction
Inoue, T
Kitagawa, O
Ochiai, O
Shiro, M
Taguchi, T
[J]. TETRAHEDRON LETTERS, 1995, 36 (51) : 9333 - 9336

← 1 2 3 4 →