Synthesis of new enantiomerically pure monoketals of p-benzoquinone with C2-symmetry

被引：10

作者：

de March, P ^{[1
]}

Figueredo, M ^{[1
]}

Font, J ^{[1
]}

Medrano, J ^{[1
]}

机构：

[1] Univ Autonoma Barcelona, Dept Quim, Bellaterra 08193, Spain

来源：

TETRAHEDRON | 1999年 / 55卷 / 25期

关键词：

D O I：

10.1016/S0040-4020(99)00400-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Several new monoketals of p-benzoquinone with the structure of 1,3-dioxaspiro[4.5]deca-6,9-dien-8-one have been synthesised in enantiopure form by the straightforward reaction of the quinone with secondary C-2-symmetric 1,2-diols. The preparation of two new enantiopure C-2-1,2-glycolsis also reported. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：7907 / 7914

页数：8

共 16 条

[1] TRANSOID HOMOALLYLIC PROTON-PROTON COUPLING-CONSTANTS [J].

BARFIELD, M ;

SPEAR, RJ ;

STERNHELL, S .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1989, 42 (05) :659-664

[2] FIRST PREPARATION OF OPTICALLY PURE KETALS OF P-BENZOQUINONE [J].

DEMARCH, P ;

ESCODA, M ;

FIGUEREDO, M ;

FONT, J ;

ALVAREZLARENA, A ;

PINIELLA, JF .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (12) :3895-3897

[3]

deMarch P, 1997, AN QUIM, V93, P81

[4] Asymmetric induction in the cycloaddition of a masked p-benzoquinone to cyclic nitrones [J].

deMarch, P ;

Escoda, M ;

Figueredo, M ;

Font, J ;

AlvarezLarena, A ;

Piniella, JF .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (22) :7781-7787

[5] SYNTHESIS OF CHIRAL NONRACEMIC DIOLS VIA NUCLEOPHILIC OPENING OF (S,S)-1,2,3,4-DIEPOXYBUTANE [J].

DEVINE, PN ;

OH, T .

TETRAHEDRON LETTERS, 1991, 32 (07) :883-886

[6] 1,4-BISMETHANESULFONATES OF STEREOISOMERIC BUTANETETRAOLS + RELATED COMPOUNDS [J].

FEIT, PW .

JOURNAL OF MEDICINAL CHEMISTRY, 1964, 7 (01) :14-+

[7] STEREOSELECTIVE SYNTHESIS OF ALCOHOLS .31. STEREOSELECTIVE C-C BOND FORMATION USING CHIRAL Z-PENTENYLBORONATES [J].

HOFFMANN, RW ;

DITRICH, K ;

KOSTER, G ;

STURMER, R .

CHEMISCHE BERICHTE, 1989, 122 (09) :1783-1789

[8]

JONES GB, 1995, SYNTHESIS-STUTTGART, P475

[9]

MAFFEI M, 1988, NEW J CHEM, V12, P923

[10]

MASH EA, 1989, ORG SYNTH, V68, P92

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