NEW APPROACHES IN ASYMMETRIC-SYNTHESIS USING GAMMA-ALKOXYBUTENOLIDES

被引：61

作者：

FERINGA, BL

DELANGE, B

JANSEN, JFGA

DEJONG, JC

LUBBEN, M

FABER, W

SCHUDDE, EP

机构：

[1] Department of Organic and Molecular Inorganic Chemistry, University of Groningen, 9747 AG, Groningen

来源：

PURE AND APPLIED CHEMISTRY | 1992年 / 64卷 / 12期

关键词：

D O I：

10.1351/pac199264121865

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The synthesis of a new class of auxiliary based chiral synthons, gamma-alkoxy-2(5H)-furanones, is described. The multifunctional compounds enter a variety of asymmetric transformations leading to acyclic- and cyclic-products with up to four new stereogenic centers in a single operation with stereoselectivities exceeding 98%. Applications in new routes to an enantiomerically pure beta-lactam and lignans are given.

引用

页码：1865 / 1871

页数：7

共 29 条

[1] ASYMMETRIC DIELS-ALDER REACTIONS WITH 5-MENTHYLOXY-2(5H)-FURANONE
DEJONG, JC
VANBOLHUIS, F
FERINGA, BL
[J]. TETRAHEDRON-ASYMMETRY, 1991, 2 (12) : 1247 - 1262
[2] SYNTHESIS OF ENANTIOMERICALLY PURE BICYCLIC AND TRICYCLIC LACTONES WITH QUATERNARY CHIRAL CENTERS
DEJONG, JC
FERINGA, BL
[J]. TETRAHEDRON LETTERS, 1989, 30 (51) : 7239 - 7240
[3] ASYMMETRIC-SYNTHESIS OF DECALINES AND HEXAHYDROINDANES
DEJONG, JC
JANSEN, JFGA
FERINGA, BL
[J]. TETRAHEDRON LETTERS, 1990, 31 (21) : 3047 - 3050
[4] DEJONG JC, 1990, THESIS U GRONINGEN N
[5] ASYMMETRIC 1,3-DIPOLAR CYCLO-ADDITIONS TO 5-MENTHYLOXY-2[5H]-FURANONES
DELANGE, B
FERINGA, BL
[J]. TETRAHEDRON LETTERS, 1988, 29 (41) : 5317 - 5320
[6] ASYMMETRIC 1,4-ADDITIONS TO 5-ALKOXY-2(5H)-FURANONES ENANTIOSELECTIVE SYNTHESIS AND ABSOLUTE-CONFIGURATION DETERMINATION OF BETA-AMINO-GAMMA-BUTYROLACTONES AND AMINO DIOLS
DELANGE, B
VANBOLHUIS, F
FERINGA, BL
[J]. TETRAHEDRON, 1989, 45 (21) : 6799 - 6818
[7] FERINGA BL, 1987, RECL TRAV CHIM PAY B, V106, P469
[8] CHIROPTICAL MOLECULAR SWITCH
FERINGA, BL
JAGER, WF
DELANGE, B
MEIJER, EW
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (14) : 5468 - 5470
[9] A DYNAMIC CHEMI-LUMINESCENT PROCESS - CYCLIC AND ACYCLIC PATHWAYS IN THE PHOTO-OXIDATIVE DECARBONYLATION OF 5-METHYLFURFURAL
FERINGA, BL
BUTSELAAR, RJ
[J]. TETRAHEDRON LETTERS, 1983, 24 (11) : 1193 - 1196
[10] ASYMMETRIC 1,4-ADDITIONS TO 5-ALKOXY-2(5H)-FURANONES - AN EFFICIENT SYNTHESIS OF (R)-3,4-EPOXY-1-BUTANOL AND (S)-3,4-EPOXY-1-BUTANOL
FERINGA, BL
DELANGE, B
[J]. TETRAHEDRON, 1988, 44 (23) : 7213 - 7222

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