New chiral hypervalent iodine compounds in asymmetric synthesis

被引：137

作者：

Hirt, UH

Spingler, B

Wirth, T

机构：

[1] Univ Basel, Inst Organ Chem, CH-4056 Basel, Switzerland

[2] Univ Basel, Inst Anorgan Chem, Lab Kristallog, CH-4056 Basel, Switzerland

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1998年 / 63卷 / 22期

关键词：

D O I：

10.1021/jo980475x

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of new chiral hypervalent iodine compounds 3 and their use in asymmetric oxidative functionalizations are described. The substituents in the chiral moiety and the stereoelectronic properties of the reagents 3, as well as the reaction conditions, have been optimized. Chiral hypervalent iodine compounds 3 have been investigated in the asymmetric dioxytosylation of styrene and in the alpha-oxytosylation of propiophenone as test reactions. X-ray structural analysis of some reagents shows an interaction between the chiral moiety and the iodine resulting in stereoselectivities up to 53% ee in the products.

引用

收藏

页码：7674 / 7679

页数：6

相关论文

共 35 条

[1]

ALOCK NW, 1979, J CHEM SOC DA, P854

[2] ZIRCONOCENE(ISO-BUTYL) CHLORIDE - INSITU GENERATION OF A ZIRCONOCENE(METHYL) CHLORIDE EQUIVALENT FOR USE IN ORGANIC-SYNTHESIS [J].

BARR, KJ ;

WATSON, BT ;

BUCHWALD, SL .

TETRAHEDRON LETTERS, 1991, 32 (40) :5465-5468

[3] CHIRAL SYNTHESIS VIA ORGANOBORANES .14. SELECTIVE REDUCTIONS .41. DIISOPINOCAMPHEYLCHLOROBORANE, AN EXCEPTIONALLY EFFICIENT CHIRAL REDUCING AGENT [J].

BROWN, HC ;

CHANDRASEKHARAN, J ;

RAMACHANDRAN, PV .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (05) :1539-1546

[4] KINETIC RESOLUTION STRATEGIES .2. ENHANCED ENANTIOMERIC EXCESSES AND YIELDS FOR THE FASTER REACTING ENANTIOMER IN LIPASE-MEDIATED KINETIC RESOLUTIONS [J].

BROWN, SM ;

DAVIES, SG ;

DESOUSA, JAA .

TETRAHEDRON-ASYMMETRY, 1993, 4 (05) :813-822

[5] A GENERAL-METHOD FOR THE PREPARATION OF ZIRCONOCENE COMPLEXES OF SUBSTITUTED BENZYNES - INSITU GENERATION, COUPLING REACTIONS, AND USE IN THE SYNTHESIS OF POLYFUNCTIONALIZED AROMATIC-COMPOUNDS [J].

BUCHWALD, SL ;

WATSON, BT ;

LUM, RT ;

NUGENT, WA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (23) :7137-7141

[6] A GENERAL ENANTIOSELECTIVE SYNTHESIS OF ALPHA-ARYLETHYLAMINES [J].

CHEN, CP ;

PRASAD, K ;

REPIC, O .

TETRAHEDRON LETTERS, 1991, 32 (49) :7175-7178

[7] ENAMTIOMERIC PURITY OF PHENYLETHYLENE GLYCOLE AND RELIABILITY OF PHENYLGLYOXYLATE ASYMMETRIC REDUCTIONS IN CONFIGURATIONAL ASSIGNMENTS [J].

DALE, JA ;

MOSHER, HS .

JOURNAL OF ORGANIC CHEMISTRY, 1970, 35 (11) :4002-&

[8] SYNTHESES OF ZINDOXIFENE AND ANALOGS BY TITANIUM-INDUCED OXO-AMIDE COUPLING [J].

FURSTNER, A ;

JUMBAM, DN ;

SEIDEL, G .

CHEMISCHE BERICHTE, 1994, 127 (06) :1125-1130

[9] SYNTHETIC STUDIES ON MORPHINE-BASED ANALGESICS - INTRAMOLECULAR DIELS-ALDER APPROACH TO 4A-ARYLDECAHYDROISOQUINOLINES [J].

HANDA, S ;

JONES, K ;

NEWTON, CG .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (12) :1623-1633

[10] PREPARATION OF [HYDROXY(((+)-10-CAMPHORSULFONYL)OXY)IODO]BENZENE AND ITS REACTIVITY TOWARD CARBONYL-COMPOUNDS [J].

HATZIGRIGORIOU, E ;

VARVOGLIS, A ;

BAKOLACHRISTIANOPOULOU, M .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (01) :315-318

← 1 2 3 4 →