Tri- and tetrasubstituted α-fluorocyclohexanones with enantiomeric excesses in the range of 97-100%

被引：25

作者：

Solladié-Cavallo, A

Jierry, L

Bouérat, L

Taillasson, P

机构：

[1] Univ Strasbourg 1, CNRS, ECPM, Lab Stereochim Organomet Associe, F-67087 Strasbourg, France

[2] Sylachim Finorga, F-38670 Chasse Sur Rhone, France

来源：

TETRAHEDRON-ASYMMETRY | 2001年 / 12卷 / 06期

关键词：

D O I：

10.1016/S0957-4166(01)00118-5

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The alpha -fluorinated trisubstituted ketones (2S,5R)-(-1-7-Ia. (2R,5R)-(+)-7-IIe. (2S,5R)-(-)-8-Ia and (2R.5R)-(+)-8-IIe were synthesised from (+)-dihydrocarvone (99%, (R)-configuration at C-5) and fully characterised. alpha -Fluorinated tetrasubstituted ketones (-)-9-Ia, (+)-9-Ia, (+)-9-IIa and (+)-10-Ia having e.e.s of greater than or equal to 97% were synthesised as racemates from 3-methyl cyclo-hexenone then resolved into the pure enantiomers using chiral HPLC and fully characterised. (C) 2001 Published by Elsevier Science Ltd.

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页码：883 / 891

页数：9

相关论文

共 20 条

[1] Transition state stereoelectronics in alkene epoxidations by fluorinated dioxiranes [J].

Armstrong, A ;

Washington, I ;

Houk, KN .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (26) :6297-6298

[2] Catalytic enantioselective epoxidation of alkenes with a tropinone-derived chiral ketone [J].

Armstrong, A ;

Hayter, BR .

CHEMICAL COMMUNICATIONS, 1998, (05) :621-622

[3] Alkene epoxidation catalyzed by bicyclo[3.2.1]octan-3-ones: effects of structural modifications on catalyst efficiency and epoxidation enantioselectivity [J].

Armstrong, A ;

Hayter, BR ;

Moss, WO ;

Reeves, JR ;

Wailes, JS .

TETRAHEDRON-ASYMMETRY, 2000, 11 (10) :2057-2061

[4] EPOXIDATION WITH DIOXIRANES DERIVED FROM 2-FLUORO-2-SUBSTITUTED-1-TETRALONES AND 2-FLUORO-2-SUBSTITUTED-1-INDANONES [J].

BROWN, DS ;

MARPLES, BA ;

SMITH, P ;

WALTON, L .

TETRAHEDRON, 1995, 51 (12) :3587-3606

[5] A NEW PRACTICAL SYNTHESIS OF SILYL ENOL ETHERS .1. FROM SIMPLE ALDEHYDES AND KETONES [J].

CAZEAU, P ;

DUBOUDIN, F ;

MOULINES, F ;

BABOT, O ;

DUNOGUES, J .

TETRAHEDRON, 1987, 43 (09) :2075-2088

[6] ENANTIOSELECTIVE EPOXIDATION OF UNFUNCTIONALIZED ALKENES USING DIOXIRANES GENERATED IN-SITU [J].

CURCI, R ;

D'ACCOLTI, L ;

FIORENTINO, M ;

ROSA, A .

TETRAHEDRON LETTERS, 1995, 36 (32) :5831-5834

[7] Catalytic epoxidation of alkenes with oxone .2. Fluoro ketones [J].

Denmark, SE ;

Wu, ZC ;

Crudden, CM ;

Matsuhashi, H .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (24) :8288-8289

[8]

Denmark SE, 1999, SYNLETT, P847

[9]

Eliel E.L., 1994, Stereochemistry of Organic Compounds

[10] CONFORMATIONAL-ANALYSIS .40. CONFORMATION OF 1-METHYL-1-PHENYLCYCLOHEXANE AND THE CONFORMATIONAL ENERGIES OF THE PHENYL AND VINYL GROUPS [J].

ELIEL, EL ;

MANOHARAN, M .

JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (09) :1959-1962