PHENYLSULFONYL-SUBSTITUTED 5-ALKOXY-2(5H)-FURANONES - A NEW CLASS OF HIGHLY REACTIVE CHIRAL DIENOPHILES

被引：18

作者：

DEJONG, JC ^{[1
]}

VANDENBERG, KJ ^{[1
]}

VANLEUSEN, AM ^{[1
]}

FERINGA, BL ^{[1
]}

机构：

[1] UNIV GRONINGEN,DEPT ORGAN CHEM,NIJENBORGH 16,9747 AG GRONINGEN,NETHERLANDS

来源：

TETRAHEDRON LETTERS | 1991年 / 32卷 / 52期

关键词：

D O I：

10.1016/0040-4039(91)80582-Q

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of enantiomerically pure (5S)-5-(d-menthyloxy)-4-(phenylsulfonyl)-2(5H)-furanone (4) and the application of 4 as efficient dienophile in Diels-Alder reactions under mild conditions with enantioselectivities > 98% e.e. are described.

引用

页码：7751 / 7754

页数：4

共 13 条

[1] SYNTHESIS OF ENANTIOMERICALLY PURE BICYCLIC AND TRICYCLIC LACTONES WITH QUATERNARY CHIRAL CENTERS
DEJONG, JC
FERINGA, BL
[J]. TETRAHEDRON LETTERS, 1989, 30 (51) : 7239 - 7240
[2] ASYMMETRIC-SYNTHESIS OF DECALINES AND HEXAHYDROINDANES
DEJONG, JC
JANSEN, JFGA
FERINGA, BL
[J]. TETRAHEDRON LETTERS, 1990, 31 (21) : 3047 - 3050
[3] ASYMMETRIC 1,3-DIPOLAR CYCLO-ADDITIONS TO 5-MENTHYLOXY-2[5H]-FURANONES
DELANGE, B
FERINGA, BL
[J]. TETRAHEDRON LETTERS, 1988, 29 (41) : 5317 - 5320
[4] 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
[5] DELANGE B, 1988, TETRAHEDRON, V44, P7213
[6] FERINGA BL, 1987, RECL TRAV CHIM PAY B, V106, P469
[7] SYNTHESIS OF ENANTIOMERICALLY PURE GAMMA-(MENTHYLOXY)BUTENOLIDES AND (R)-2-METHYL-1,4-BUTANEDIOL AND (S)-2-METHYL-1,4-BUTANEDIOL
FERINGA, BL
DELANGE, B
DEJONG, JC
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (10) : 2471 - 2475
[8] ASYMMETRIC DIELS-ALDER REACTIONS WITH A CHIRAL MALEIC-ANHYDRIDE ANALOG, 5-(1-MENTHYLOXY)-2(5H)-FURANONE
FERINGA, BL
DEJONG, JC
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (05) : 1125 - 1127
[9] ASYMMETRIC 1,4-ADDITIONS TO GAMMA-MENTHYLOXYBUTENOLIDES .3. ENANTIOSELECTIVE SYNTHESIS OF (-)EUDESMIN
JANSEN, JFGA
FERINGA, BL
[J]. TETRAHEDRON LETTERS, 1991, 32 (27) : 3239 - 3242
[10] PREPARATION OF DIMETHYL 2-(PHENYLTHIO)MALEATE, DIMETHYL 2-(PHENYLTHIO)FUMARATE, AND THEIR SULFOXIDES
KAYDOS, JA
SMITH, DL
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (07) : 1096 - 1099

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