Stereoselective intra- and intermolecular [2+2] photocycloaddition reactions of 4-(2'-aminoethyl)quinolones

被引：25

作者：

Brandes, S ^{[1
]}

Selig, P ^{[1
]}

Bach, T ^{[1
]}

机构：

[1] Tech Univ Munich, Lehrstuhl Organ Chem 1, D-85747 Garching, Germany

来源：

SYNLETT | 2004年 / 14期

关键词：

asymmetric synthesis; cycloadditions; cyclobutanes; diastercoselectivity; photochemistry; quinolones;

D O I：

10.1055/s-2004-834817

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The 4-(2'-aminoethyl)quinolones 6, 8 and 9 were prepared starting from 4-(2'-bromoethyl)quinolone (4) in two steps and overall yields of 56-93%. They underwent inter- and intramolecular [2+2] photocycloaddition reactions with an alkene to provide the cyclobutanes 1-3 in racemic form (61-89% yield). The photochemical reaction proceeded with very good chemo-, regio-and stereo-selectivity. It was in one case (8b --> 2b) also performed enantioselectively (93% ee).

引用

页码：2588 / 2590

页数：3

共 29 条

[1]

[Anonymous], MOL SUPRAM PHOTOCHEM

[2]

[Anonymous], ORG PHOTOCHEM

[3]

[Anonymous], ADV PHOTOCHEM

[4] Highly enantioselective intra- and intermolecular [2+2] photocycloaddition reactions of 2-quinolones mediated by a chiral lactam host: Host-guest interactions, product configuration, and the origin of the stereoselectivity in solution [J].

Bach, T ;

Bergmann, H ;

Grosch, B ;

Harms, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (27) :7982-7990

[5] Enantioselective [6π]-photocyclization reaction of an acrylanilide mediated by a chiral host.: Interplay between enantioselective ring closure and enantioselective protonation [J].

Bach, T ;

Grosch, B ;

Strassner, T ;

Herdtweck, E .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (03) :1107-1116

[6] Synthesis of enantiomerically pure 1,5,7-trimethyl-3-azabicyclo[3.3.1]nonan-2-ones as chiral host compounds for enantioselective photochemical reactions in solution [J].

Bach, T ;

Bergmann, H ;

Grosch, B ;

Harms, K ;

Herdtweck, E .

SYNTHESIS-STUTTGART, 2001, (09) :1395-1405

[7]

Bach T, 1998, SYNTHESIS-STUTTGART, P683

[8] An enantiomerically pure 1,5,7-trimethyl-3-azabicyclo[3.3.1]nonan-2-one as 1H NMR shift reagent for the ee determination of chiral lactams, quinolones, and oxazolidinones [J].

Bergmann, H ;

Grosch, B ;

Sitterberg, S ;

Bach, T .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (03) :970-973

[9] PHOTOCYCLOADDITION OF CYCLOHEXENE TO CARBOSTYRILS [J].

BUCHARDT, O ;

CHRISTENSEN, JJ ;

HARRIT, N .

ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1976, 30 (03) :189-192

[10] PHOTOCHEMICAL CYCLOADDITION OF CYCLOHEXENONE AND CYCLOPENTENONE TO CONJUGATED DIENES [J].

CANTRELL, TS .

JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (21) :3063-3070

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