Synthesis of novel C2-symmetrical chiral sulfides and their utility in asymmetric epoxidation of aldehydes

被引：6

作者：

Ishizaki, M ^{[1
]}

Hoshino, O ^{[1
]}

机构：

[1] Sci Univ Tokyo, Fac Pharmaceut Sci, Shinjuku Ku, Tokyo 162, Japan

来源：

CHIRALITY | 2003年 / 15卷 / 04期

关键词：

asymmetric epoxidation; chiral sulfides; aromatic sulfide; silyl ether; tartaric acid;

D O I：

10.1002/chir.10204

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Novel C-2-symmetrical chiral sulfides were synthesized from (R,R)tartaric acid and their utility in the asymmetric epoxidation of aldehydes with benzyl bromide was examined. Among the sulfides used, silyl ether-type sulfides were found to be superior to diol- and benzyl ether-type sulfides. Also, the presence of an aromatic group on the sulfide was proven to be an important factor for increasing enantioselectivity.

引用

页码：300 / 305

页数：6

共 17 条

[1] PREPARATION OF OPTICALLY-ACTIVE EPOXIDES VIA SULFUR YLIDES - ORIGIN OF THE CHIRAL INDUCTION [J].

BREAU, L ;

DURST, T .

TETRAHEDRON-ASYMMETRY, 1991, 2 (05) :367-370

[2] PREPARATION OF OPTICALLY-ACTIVE STILBENE OXIDES VIA SULFONIUM SALTS DERIVED FROM C-2 SYMMETRIC THIOLANES [J].

BREAU, L ;

OGILVIE, WW ;

DURST, T .

TETRAHEDRON LETTERS, 1990, 31 (01) :35-38

[3] Synthesis and reactivity of cationic iridium(I) complexes of cycloocta-1,5-diene and chiral dithioether ligands. Application as catalyst precursors in asymmetric hydrogenation [J].

Dieguez, M ;

Orejon, A ;

Masdeu-Bulto, AM ;

Echarri, R ;

Castillon, S ;

Claver, C ;

Ruiz, A .

JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1997, (23) :4611-4618

[4] CAMPHORYL SULFIDE AS A CHIRAL AUXILIARY AND A MEDIATOR FOR ONE-STEP SYNTHESIS OF OPTICALLY-ACTIVE 1,2-DIARYLOXIRANES [J].

FURUKAWA, N ;

SUGIHARA, Y ;

FUJIHARA, H .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (17) :4222-4224

[5] 2-Alkenyl dioxolanylium cations, new reactive dienophiles in low temperature asymmetric Diels-Alder reactions [J].

Haudrechy, A ;

Picoul, W ;

Langlois, Y .

TETRAHEDRON-ASYMMETRY, 1997, 8 (01) :139-148

[6]

Hayakawa R, 1999, SYNLETT, P1328

[7] Asymmetric epoxidation of aldehydes catalyzed by new C2-symmetrical chiral sulfide [J].

Ishizaki, M ;

Hoshino, O .

HETEROCYCLES, 2002, 57 (08) :1399-1402

[8] A simple C2 symmetrical sulfide for a one-pot asymmetric conversion of aldehydes into oxiranes [J].

Julienne, K ;

Metzner, P ;

Henryon, V ;

Greiner, A .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (13) :4532-4534

[9]

KATSUKI T, 1999, ASYMMETRIC C H OXIDA, V2

[10] Preparation of enantiomerically enriched (2R,3R)- or (2S,3S)-trans-2,3-diaryloxiranes via camphor-derived sulfonium ylides [J].

Li, AH ;

Dai, LX ;

Hou, XL ;

Huang, YZ ;

Li, FW .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (02) :489-493

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