Complete diastereofacial selective cycloaddition of new sulfinyl dienophiles (Ss)-and (Rs)-(-)menthyl alpha-(2-methoxyphenylsulfoxyl)acylate with anthracene under chelation control

被引：5

作者：

Chau, TY ^{[1
]}

Lin, HC ^{[1
]}

Hu, WH ^{[1
]}

机构：

[1] CHENGDU INST ORGAN CHEM, UNION LAB ASYMMETR SYNTH, CHENGDU 610041, PEOPLES R CHINA

来源：

SYNTHETIC COMMUNICATIONS | 1996年 / 26卷 / 10期

关键词：

D O I：

10.1080/00397919608003539

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

New sulfinyldienophiles (Ss)- and (Rs)- (-)menthyl alpha-(2-methoxyphenylsulfoxyl)acylate were prepared. Cycloadditions with anthracene in dichloromethane proceeded with complete diastereoselectivity under chelation control. Chirality at sulfur controlled diastereofacial selectivity.

引用

页码：1867 / 1874

页数：8

共 10 条

[1] CONTROL OF STEREOCHEMISTRY BY SULFOXIDE CHIRALITY IN DIELS-ALDER REACTIONS OF 1-METHOXY-3-ALKYLSULFINYLBUTADIENES [J].

ADAMS, H ;

JONES, DN ;

AVERSA, MC ;

BONACCORSI, P ;

GIANNETTO, P .

TETRAHEDRON LETTERS, 1993, 34 (40) :6481-6484

[2] OPTICALLY-ACTIVE 2-PARA-TOLYLSULFINYLACRYLATE - A NOVEL CHIRAL DIENOPHILE WHICH EXHIBITS HIGH REACTIVITY AND DIASTEREOSELECTIVITY [J].

ARAI, Y ;

KUWAYAMA, S ;

TAKEUCHI, Y ;

KOIZUMI, T .

TETRAHEDRON LETTERS, 1985, 26 (50) :6205-6208

[3] HOMOCHIRAL 1-METHOXY-3-SULFINYL-1,3-BUTADIENES DERIVED FROM 10-MERCAPTOISOBORNEOL [J].

AVERSA, MC ;

BONACCORSI, P ;

GIANNETTO, P ;

JAFARI, SMA ;

JONES, DN .

TETRAHEDRON-ASYMMETRY, 1992, 3 (06) :701-704

[4] AN EASY SYNTHESIS OF CHIRAL SULFINYL ALLYLIC BROMIDES AND THEIR USE IN THE PREPARATION OF (R)S-2-P-TOLYLSULFINYL-1,3-ALKADIENES AND (S)S-2-P-TOLYLSULFINYL-1,3-ALKADIENES [J].

BONFAND, E ;

GOSSELIN, P ;

MAIGNAN, C .

TETRAHEDRON-ASYMMETRY, 1993, 4 (07) :1667-1676

[5] 1ST SYNTHESES OF CHIRAL 2-SULFINYLBUTADIENES [J].

BONFAND, E ;

GOSSELIN, P ;

MAIGNAN, C .

TETRAHEDRON LETTERS, 1992, 33 (17) :2347-2348

[6] SELF-INDUCED DIASTEREOSELECTIVE OXIDATION OF VINYL SULFIDES BEARING A CHIRAL HYDROXY GROUP AS A WAY OF PREPARATION OF OPTICALLY-ACTIVE SULFINYL DIENOPHILES AND THEIR USE IN THE ASYMMETRIC DIELS-ALDER REACTION TO CYCLOPENTADIENE [J].

DELUCCHI, O ;

LUCCHINI, V ;

MARCHIORO, C ;

VALLE, G ;

MODENA, G .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (09) :1457-1466

[7] INTRAMOLECULAR LEWIS ACID-CATALYZED ASYMMETRIC HETERO-DIELS-ALDER REACTIONS WITH DIENES BEARING CHIRAL SULFINYL GROUPS [J].

HIROI, K ;

UMEMURA, M ;

FUJISAWA, A .

TETRAHEDRON LETTERS, 1992, 33 (47) :7161-7164

[8] A DISPROOF OF KAHN-HEHRE PROPOSAL ON THE GROUND-STATE CONFORMATIONS AND THE STERIC COURSE OF THE DIELS-ALDER REACTION OF VINYL SULFOXIDES [J].

KOIZUMI, T ;

ARAI, Y ;

TAKAYAMA, H ;

KURIYAMA, K ;

SHIRO, M .

TETRAHEDRON LETTERS, 1987, 28 (32) :3689-3692

[9] HIGHLY DIASTEREOSELECTIVE DIELS-ALDER REACTIONS WITH (R)-ETHOXY PARA-TOLY VINYL SULFONIUM TETRAFLUOROBORATE [J].

RONAN, B ;

KAGAN, HB .

TETRAHEDRON-ASYMMETRY, 1991, 2 (01) :75-90

[10] ASYMMETRIC 1,3-DIPOLAR CYCLOADDITION OF CHIRAL SULPHINYLETHENES WITH 1-METHYL-3-OXIDOPYRIDINIUM AND SOME NITRONES [J].

TAKAHASHI, T ;

FUJII, A ;

SUGITA, J ;

HAGI, T ;

KITANO, K ;

ARAI, Y ;

KOIZUMI, T ;

SHIRO, M .

TETRAHEDRON-ASYMMETRY, 1991, 2 (12) :1379-1390

← 1 →