Highly diastereoselective 5-hexenyl radical cyclizations with Lewis acids and carbohydrate scaffolds

被引：25

作者：

Enholm, EJ ^{[1
]}

Cottone, JS ^{[1
]}

Allais, F ^{[1
]}

机构：

[1] Univ Florida, Dept Chem, Gainesville, FL 32611 USA

来源：

ORGANIC LETTERS | 2001年 / 3卷 / 02期

关键词：

D O I：

10.1021/ol006651h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Carbohydrates as removable chiral scaffolds for free redical cyclizations were examined for the first time, This investigation illustrates the utility of two inexpensive carbohydrate derivatives as sources of asymmetry for 5-hexenyl radical cyclizations, Diastereomeric ratios as high as 100:1 were achieved with an ester-appended (+) isosorbide hexose and 70:1 for a diol protected D-xylose pentose, Temperature dependence, Lewis acids, and solvents were all examined, By correlation with known compounds, the newly generated chiral centers were of the (S)-configuration.

引用

收藏

页码：145 / 147

页数：3

相关论文

共 19 条

[1] Diastereoselective chelation-controlled radical cyclization of chiral oxazolidinone-derived 2-alkenamides and modeling of the transition state [J].

Badone, D ;

Bernassau, JM ;

Cardamone, R ;

Guzzi, U .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1996, 35 (05) :535-538

[2] USE OF PYRIDINIUM CHLOROCHROMATE AS METHYLENE OXIDANT IN 5,6-DIHYDROPYRANS - A PRACTICAL, ONE-STEP PREPARATION OF THE ANHYDROMEVALONOLACTONE [J].

BONADIES, F ;

DIFABIO, R ;

BONINI, C .

JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (09) :1647-1649

[3]

JONES JB, 1978, J AM CHEM SOC, V16, P5199

[4]

Leonard J, 1998, EUR J ORG CHEM, V1998, P2051

[5] Asymmetric Diels-Alder: Monobenzylated isosorbide and isomannide as highly effective chiral auxiliaries [J].

Loupy, A ;

Monteux, D .

TETRAHEDRON LETTERS, 1996, 37 (39) :7023-7026

[6] Lewis acid-promoted atom-transfer free radical additions [J].

Mero, CL ;

Porter, NA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (22) :5155-5160

[7] Construction of chiral quaternary carbon centers by catalytic enantioselective radical-mediated allylation of alpha-iodolactones using allyltributyltin in the presence of a chiral Lewis acid [J].

Murakata, M ;

Jono, T ;

Mizuno, Y ;

Hoshino, O .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (48) :11713-11714

[8] A SIMPLE PREPARATION OF (R)-(2-CYCLOPENTENYL)ACETIC-ACID AND (R)-(2-CYCLOHEXENYL)ACETIC ACID USING BETA-DIASTEREOSELECTIVE RADICAL CYCLIZATION IN THE PRESENCE OF LEWIS-ACID [J].

NISHIDA, M ;

HAYASHI, H ;

YAMAURA, Y ;

YANAGINUMA, E ;

YONEMITSU, O ;

NISHIDA, A ;

KAWAHARA, N .

TETRAHEDRON LETTERS, 1995, 36 (02) :269-272

[9] LEWIS ACID-PROMOTED DIASTEREOSELECTIVE RADICAL CYCLIZATION USING CHIRAL ALPHA,BETA-UNSATURATED ESTERS [J].

NISHIDA, M ;

UEYAMA, E ;

HAYASHI, H ;

OHTAKE, Y ;

YAMAURA, Y ;

YANAGINUMA, E ;

YONEMITSU, O ;

NISHIDA, A ;

KAWAHARA, N .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (14) :6455-6456

[10] TRIALKYLBORANE AS AN INITIATOR AND TERMINATOR OF FREE-RADICAL REACTIONS - FACILE ROUTES TO BORON ENOLATES VIA ALPHA-CARBONYL RADICALS AND ALDOL REACTION OF BORON ENOLATES [J].

NOZAKI, K ;

OSHIMA, K ;

UTIMOTO, K .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1991, 64 (02) :403-409