Novel synthesis of chiral, enantiomerically pure thiodiglycols and diglycols

被引：19

作者：

Christoffers, J ^{[1
]}

Rössler, U ^{[1
]}

机构：

[1] Tech Univ Berlin, Inst Organ Chem, Sekretariat C 3, D-10623 Berlin, Germany

来源：

TETRAHEDRON-ASYMMETRY | 1998年 / 9卷 / 13期

关键词：

D O I：

10.1016/S0957-4166(98)00224-9

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Natural cx-hydroxy acids have been converted in a sequence of O-protection, reduction, O-activation, thioether and ether formation and deprotection to chiral, non-racemic beta, beta'-dihydroxy thioethers 1a, 1b and ether 1c. Overall yields are excellent (75%). In an attempt to synthesize the respective dihydroxy ether Id derived from mandelic acid 1,3-dioxolane derivatives 7 were obtained. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：2349 / 2357

页数：9

共 31 条

[1]

[Anonymous], 1895, BER DTSCH CHEM GES

[2] Tripod ligand with cyclopentadienyl donor group:: Synthesis and reactivity of complexes of the type CH3C(CH2-η5-C5H4)(CH2PR2)(CH2PR2′)FeCl [J].

Antelmann, B ;

Huttner, G ;

Vogelgesang, J ;

Walter, O ;

Winterhalter, U .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1997, 549 (1-2) :139-148

[3]

AOKI S, 1992, HETEROCYCLES, V33, P493

[4]

BERENS U, 1991, SYNTHESIS-STUTTGART, P832

[5] TRIPHENYLSILANETHIOL - A SOLID H2S EQUIVALENT IN THE RING-OPENING OF EPOXIDES [J].

BRITTAIN, J ;

GAREAU, Y .

TETRAHEDRON LETTERS, 1993, 34 (21) :3363-3366

[6]

Brunner H, 1993, HDB ENANTIOSELECTIVE, V2

[7] Syntheses and structures of palladium(II) and platinum(II) complexes with tridentate (Ph2PCH2CH2CH2)(2)S and its arsenic analogue [J].

Cheng, CR ;

Leung, PH ;

Mok, KF .

INORGANICA CHIMICA ACTA, 1997, 260 (02) :137-143

[8]

Christoffers J, 1997, LIEBIGS ANN-RECL, P1353

[9] The action of the chlorides of sulphur on substituted ethylenes - The action of propylene on sulphur monochloride and the synthesis of beta beta'-dichlorodi-n-propyl sulphide [J].

Coffey, S .

JOURNAL OF THE CHEMICAL SOCIETY, 1921, 119 :94-98

[10] ALKALI-METALS DISSOLVED IN OPTICALLY-ACTIVE SOLVENTS [J].

COOPER, KD ;

WALBORSKY, HM .

JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (10) :2110-2116

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