STEREODIVERGENT DIELS-ALDER REACTIONS EMPLOYING CYCLITOLS AS CHIRAL AUXILIARIES

被引：19

作者：

AKIYAMA, T ^{[1
]}

HORIGUCHI, N ^{[1
]}

IDA, T ^{[1
]}

OZAKI, S ^{[1
]}

机构：

[1] EHIME UNIV, FAC ENGN, DEPT APPL CHEM, MATSUYAMA, EHIME 790, JAPAN

来源：

CHEMISTRY LETTERS | 1995年 / 11期

关键词：

D O I：

10.1246/cl.1995.975

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The TiCl4 or SnCl4 mediated Diels-Alder reaction of cyclopentadiene and chiral acryloyl ester derived from chiral cyclitols proceeded with excellent diastereoselectivity in Et(2)O via re-face attack of the acrylates. In contrast, interesting changeover of the diastereofacial selectivity was observed by use of toluene or hexane as a solvent to afford the cycloadducts derived from si-face attack of the acrylates.

引用

页码：975 / 976

页数：2

共 26 条

[1] DIASTEREOSELECTIVE ADDITION OF ORGANOMETALLICS TO ALPHA-KETO ESTERS BEARING CHIRO-INOSITOL DERIVATIVES AS CHIRAL AUXILIARIES [J].

AKIYAMA, T ;

NISHIMOTO, H ;

ISHIKAWA, K ;

OZAKI, S .

CHEMISTRY LETTERS, 1992, (03) :447-450

[2] CHIRAL SYNTHESIS OF D-MYO-INOSITOL 1-PHOSPHATE STARTING FROM L-QUEBRACHITOL [J].

AKIYAMA, T ;

TAKECHI, N ;

OZAKI, S .

TETRAHEDRON LETTERS, 1990, 31 (10) :1433-1434

[3] DIASTEREOSELECTIVE REDUCTION OF ALPHA-KETO ESTERS BEARING CHIRO-INOSITOL DERIVATIVES AS CHIRAL AUXILIARIES [J].

AKIYAMA, T ;

NISHIMOTO, H ;

OZAKI, S .

TETRAHEDRON LETTERS, 1991, 32 (10) :1335-1338

[4]

AKIYAMA T, 1991, SYNLETT, P831

[5] A CHIRAL SYNTHESIS OF D-MYO-INOSITOL 1-PHOSPHATE STARTING FROM L-QUEBRACHITOL [J].

AKIYAMA, T ;

TAKECHI, N ;

OZAKI, S ;

SHIOTA, K .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1992, 65 (02) :366-372

[6] STEREODIVERGENT SYNTHESIS OF OPTICALLY-ACTIVE ALPHA-HYDROXY ACIDS VIA DIASTEREOSELECTIVE REDUCTION OF ALPHA-KETO ESTERS DERIVED FROM L-QUEBRACHITOL [J].

AKIYAMA, T ;

NISHIMOTO, H ;

KUWATA, T ;

OZAKI, S .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1994, 67 (01) :180-188

[7] SYNTHESIS OF (-)-CONDURITOL F, (+)-CONDURITOL-B, CYCLOPHELLITOL FROM L-QUEBRACHITOL [J].

AKIYAMA, T ;

SHIMA, H ;

OHNARI, M ;

OKAZAKI, T ;

OZAKI, S .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1993, 66 (12) :3760-3767

[8]

AKIYAMA T, 1994, SYNLETT, P275

[9] THE PREPARATION OF OPTICALLY-ACTIVE DELTA-2-ISOXAZOLINES VIA ADDITION OF NITRILE OXIDES TO CHIRAL ACRYLOYL ESTERS BEARING CYCLITOLS AS AUXILIARIES [J].

AKIYAMA, T ;

OKADA, K ;

OZAKI, S .

TETRAHEDRON LETTERS, 1992, 33 (39) :5763-5766

[10] A CONCISE SYNTHESIS OF (-)-CONDURITOL-F FROM L-QUEBRACHITOL VIA ALCL3-NORMAL-BU4NI MEDIATED DEMETHYLATION [J].

AKIYAMA, T ;

SHIMA, H ;

OZAKI, S .

TETRAHEDRON LETTERS, 1991, 32 (40) :5593-5596

← 1 2 3 →