A new synthetic approach to enantiomerically enriched dihydrobenzofurans: use of a hydrolytic kinetic resolution and an intramolecular epoxide ring opening protocol using 1-benzyloxy-2-oxiranylmethylbenzenes

被引：11

作者：

Bhoga, U ^{[1
]}

机构：

[1] Indian Inst Chem Technol, Organ Div, Hyderabad 500007, Andhra Pradesh, India

来源：

TETRAHEDRON LETTERS | 2005年 / 46卷 / 31期

关键词：

D O I：

10.1016/j.tetlet.2005.04.120

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel approach towards the preparation of racemic 1-benzyloxy-2-oxiranylmethylbenzenes using dimethyldioxirane and their hydrolytic kinetic resolution using (R,R)(Salen)Co(III)(OAc) (Jacobsen's catalyst) to afford the (R)-epoxides and (S)1,2-diols. enantioselectively, is described. The (R)-1-benzyloxy-2-oxiranylmethylbenzenes were then cyclized via an intramolecular epoxide opening reaction to give (S)-2-hydroxymethyl-2,3-dihydrobenzofurans. (c) 2005 Published by Elsevier Ltd.

引用

页码：5239 / 5242

页数：4

共 23 条

[1] STUDIES ON KRAMERIACEAE .7. LIGNANS FROM KRAMERIA-IXINA [J].

ACHENBACH, H ;

UTZ, W ;

USUBILLAGA, A ;

RODRIGUEZ, HA .

PHYTOCHEMISTRY, 1991, 30 (11) :3753-3757

[2] DIOXIRANES - A NEW CLASS OF POWERFUL OXIDANTS [J].

ADAM, W ;

CURCI, R ;

EDWARDS, JO .

ACCOUNTS OF CHEMICAL RESEARCH, 1989, 22 (06) :205-211

[3]

[Anonymous], ORGANIC PEROXIDES

[4] Phenylpropanoids and neolignans from Piper regnellii [J].

Benevides, PJC ;

Sartorelli, P ;

Kato, MJ .

PHYTOCHEMISTRY, 1999, 52 (02) :339-343

[5] ENT-LABDANES FROM BACCHARIS-STERNBERGIANA [J].

BOHLMANN, F ;

SCHEIDGES, C ;

ZDERO, C ;

KING, RM ;

ROBINSON, H .

PHYTOCHEMISTRY, 1984, 23 (05) :1109-1111

[6] ABSOLUTE CONFIGURATIONS OF TREMETONE + TOXOL [J].

BONNER, WA ;

BURKE, NI ;

FLECK, WE ;

ZALKOW, JH ;

SJOBERG, B ;

JOULE, JA ;

HILL, RK .

TETRAHEDRON, 1964, 20 (06) :1419-&

[7]

CURCI R, 1990, ADV OXYGENATED PROCE, V2, P1

[8] Novel esters and amides of nonsteroidal antiinflammatory carboxylic acids as antioxidants and antiproliferative agents [J].

Hellberg, MR ;

Namil, A ;

Delgado, P ;

David, KC ;

Kessler, TL ;

Graff, G ;

Haggard, KS ;

Nixon, JC .

JOURNAL OF MEDICINAL CHEMISTRY, 1999, 42 (02) :267-276

[9] NEW PHENYL PROPANOIDS HAVING WEAK PISCICIDAL ACTION AND THE RELATED COMPOUND - WUTAIENSOL, WUTAIENSAL, WUTAIALDEHYDE, AND METHYL DEMETHOXYWUTAIENSATE [J].

ISHII, H ;

ISHIKAWA, T ;

CHEN, IS ;

LU, ST .

TETRAHEDRON LETTERS, 1982, 23 (42) :4345-4348

[10] Enantioselective catalytic ring opening of epoxides with carboxylic acids [J].

Jacobsen, EN ;

Kakiuchi, F ;

Konsler, RG ;

Larrow, JF ;

Tokunaga, M .

TETRAHEDRON LETTERS, 1997, 38 (05) :773-776

← 1 2 3 →