CHIRAL GAMMA-HYDROXYSULFONES AND DELTA-HYDROXYSULFONES VIA LIPASE CATALYZED RESOLUTIONS - SYNTHESIS OF (R)(+)-4-HEXANOLIDE AND (2R,5S)-2-METHYL-5-HEXANOLIDE USING INTRAMOLECULAR ACYLATION

被引：32

作者：

JACOBS, HK ^{[1
]}

MUELLER, BH ^{[1
]}

GOPALAN, AS ^{[1
]}

机构：

[1] NEW MEXICO STATE UNIV,DEPT CHEM,LAS CRUCES,NM 88003

来源：

TETRAHEDRON | 1992年 / 48卷 / 41期

关键词：

D O I：

10.1016/S0040-4020(01)81988-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Lipase PS-30 (Amano) was found to be an effective catalyst for enantioselective transesterification of a number of racemic gamma and delta hydroxysulfones with isopropenyl acetate in ether. The intramolecular acylation of the ethyl carbonate derivatives obtained from the chiral hydroxysulfones 1d and 1b has been used for the preparation of R(+)-4-hexanolide, sex pheromone of the female dermestid beetle Trogoderma glabrum and (2R, 5S)-2-methyl-5-hexanolide, the sex pheromone of the carpenter bee.

引用

页码：8891 / 8898

页数：8

共 17 条

[1] Asymmetric synthesis of (2R,5S)-2-methyl-5-hexanolide, the sex pheromone of carpenter bee Xylocopa hirutissima
Yang, Jian-Hong
Yang, Gui-Chun
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Chen, Zu-Xing
TETRAHEDRON-ASYMMETRY, 2008, 19 (18) : 2164 - 2166
[2] A CONCISE SYNTHESIS OF (2S, 5R)-2-METHYL-5-HEXANOLIDE
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ACTA CHEMICA SCANDINAVICA, 1989, 43 (02): : 193 - 195
[3] SYNTHESES OF OPTICALLY-ACTIVE INSECT PHEROMONES, (2R,5S)-2-METHYL-5-HEXANOLIDE, (3S,11S)-3,11-DIMETHYL-2-NONACOSANONE, AND SERRICORNIN
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TETRAHEDRON LETTERS, 1987, 28 (06) : 651 - 654
[4] SYNTHESIS OF (+)-(E)-(2S,5R)-5-ACETOXY-3-HEXEN-2-OL VIA ENANTIOSELECTIVE ENZYMATIC-HYDROLYSIS - AN ENANTIODIVERGENT PALLADIUM-CATALYZED ROUTE TO (+)-CIS-2-METHYL-5-HEXANOLIDE AND (-)-CIS-2-METHYL-5-HEXANOLIDE
SCHINK, HE
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JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (05): : 1588 - 1591
[5] A CHEMOENZYMATIC APPROACH TO (R)-TETRAHYDRO-5-OXO-2-(2-HYDROXYETHYL)FURAN, A USEFUL CHIRAL SYNTHON - APPLICATION TO THE SYNTHESIS OF (S)-4-HEXANOLIDE, PHEROMONE ANTIPODE OF TROGODERMA-GLABRUM
GHOSH, SK
CHATTOPADHYAY, S
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TETRAHEDRON, 1991, 47 (18-19) : 3089 - 3094
[6] Synthesis of (2R,5S)-dihydroxymethyl-(3R,4R)-dihydroxypyrrolidine (DGDP) via stereoselective amination using chlorosulfonyl isocyanate
Kim, In Su
Kim, Sin Jung
Lee, Jae Koo
Li, Qing Ri
Jung, Young Hoon
CARBOHYDRATE RESEARCH, 2007, 342 (11) : 1502 - 1509
[7] Exploration of chiral induction on epoxides in lipase-catalyzed epoxidation of alkenes using (2R,3S,4R,5S)-(-)-2,3:4,6-di-O-isopropylidiene-2-keto-L-gulonic acid monohydrate
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TETRAHEDRON-ASYMMETRY, 2009, 20 (11) : 1295 - 1300
[8] Stereoselective synthesis of MeBmt and methyl (4R,5S)-5-isopropyl-2-phenyloxazoline-4-carboxylate by a Pd-catalyzed equilibration
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JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (20): : 6818 - 6822
[9] CARBOHYDRATE-LIKE CHIRAL SYNTHONS - PREPARATION OF (R) GAMMA-HEXANOLIDE, (5R,6S,7S) 6,7-ISOPROPYLIDENDIOXY-DELTA-OCTANOLIDE AND (+)-EXOBREVICOMIN FROM (2S,3S,4R) 2,3-ISOPROPYLIDENDIOXY-4-BENZYLOXYHEPT-6-ENE
FUGANTI, C
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PEDROCCHIFANTONI, G
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TETRAHEDRON LETTERS, 1983, 24 (35) : 3753 - 3756
[10] Stereocontrolled transformation of nitrohexofuranoses into cyclopentylamines via 2-oxabicyclo[2.2.1]heptanes. IV: Synthesis of enantiopure methyl (1S,2R,3R,4R,5S)-5-benzyloxycarbonylamino-2,3-isopropylidenedioxy-4-methoxycyclopentanecarboxylate
Fernandez, Fernando
Estevez, Amalia M.
Estevez, Juan C.
Estevez, Ramon J.
TETRAHEDRON-ASYMMETRY, 2009, 20 (6-8) : 892 - 896

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