Asymmetric synthesis of tetrahydrofurans by competitive [1,2]-phenylsulfanyl (PhS) migrations under thermodynamic control

被引：7

作者：

Caggiano, L

Fox, DJ

House, D

Jones, ZA

Kerr, F

Warren, S

机构：

[1] Univ Cambridge, Chem Lab, Cambridge CB2 1EW, England

[2] Univ Milan, Dipartimento Chim Organ & Ind, I-20133 Milan, Italy

[3] Dyson Perrins Lab, Oxford 0X1 3QY, England

[4] AstraZeneca, Macclesfield SK10 2NA, Cheshire, England

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 2002年 / 23期

关键词：

D O I：

10.1039/b208556a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Triols were prepared in enantiomerically enriched form by a short route that included a Sharpless asymmetric dihydroxylation; treatment of these triols with toluene-p-sulfonic acid gave THFs as thermodynamic products.

引用

页码：2634 / 2645

页数：12

共 35 条

[21] Reagent-controlled stereoselective iodolactonizations [J].

Haas, J ;

Piguel, S ;

Wirth, T .

ORGANIC LETTERS, 2002, 4 (02) :297-300

[22] Asymmetric synthesis of tetrahydrofurans and tetrahydropyrans with competitive [1,2]-phenylsulfanyl (PhS) migrations (I): thermodynamic control [J].

House, D ;

Kerr, F ;

Warren, S .

CHEMICAL COMMUNICATIONS, 2000, (18) :1779-1780

[23] Scope and limitation of the [1,2]-phenylsulfanyl (PhS) migration in the asymmetric synthesis of tetrahydrofurans and tetrahydropyrans from common triol precursors [J].

House, D ;

Kerr, F ;

Warren, S .

CHEMICAL COMMUNICATIONS, 2000, (18) :1783-1784

[24] CATALYTIC ASYMMETRIC DIHYDROXYLATION [J].

KOLB, HC ;

VANNIEUWENHZE, MS ;

SHARPLESS, KB .

CHEMICAL REVIEWS, 1994, 94 (08) :2483-2547

[25] GAMMA-LITHIOALKOXIDES VIA REDUCTIVE LITHIATION OF OXETANES BY AROMATIC RADICAL-ANIONS [J].

MUDRYK, B ;

COHEN, T .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (24) :5657-5659

[26] Regiochemical control in intramolecular cyclization of methylene-interrupted epoxydiols [J].

Narayan, RS ;

Sivakumar, M ;

Bouhlel, E ;

Borhan, B .

ORGANIC LETTERS, 2001, 3 (16) :2489-2492

[27] ELECTROSTATIC MODULATION OF HYDROXYL GROUP IONIZATION IN ACIDIC MEDIA - EVIDENCE FOR THE COMPETITIVE OPERATION OF INTRAMOLECULAR SN2 REACTIONS [J].

NEGRI, JT ;

PAQUETTE, LA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (23) :8835-8841

[28] STEREOCHEMICALLY CONTROLLED COMPETITIVE CYCLIZATIONS WITH PHENYLTHIO MIGRATION IN THE SYNTHESIS OF CYCLIC ETHERS [J].

SANSBURY, FH ;

WARREN, S .

TETRAHEDRON LETTERS, 1992, 33 (04) :539-542

[29] NEW LIGANDS DOUBLE THE SCOPE OF THE CATALYTIC ASYMMETRIC DIHYDROXYLATION OF OLEFINS [J].

SHARPLESS, KB ;

AMBERG, W ;

BELLER, M ;

CHEN, H ;

HARTUNG, J ;

KAWANAMI, Y ;

LUBBEN, D ;

MANOURY, E ;

OGINO, Y ;

SHIBATA, T ;

UKITA, T .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (15) :4585-4588

[30] THE OSMIUM-CATALYZED ASYMMETRIC DIHYDROXYLATION - A NEW LIGAND CLASS AND A PROCESS IMPROVEMENT [J].

SHARPLESS, KB ;

AMBERG, W ;

BENNANI, YL ;

CRISPINO, GA ;

HARTUNG, J ;

JEONG, KS ;

KWONG, HL ;

MORIKAWA, K ;

WANG, ZM ;

XU, DQ ;

ZHANG, XL .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (10) :2768-2771

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