Efficient synthesis of chiral α- and β-hydroxy amides:: Application to the synthesis of (R)-fluoxetine

被引：84

作者：

Kakei, H ^{[1
]}

Nemoto, T ^{[1
]}

Ohshima, T ^{[1
]}

Shibasaki, M ^{[1
]}

机构：

[1] Univ Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, Tokyo 1130033, Japan

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2004年 / 43卷 / 03期

关键词：

asymmetric synthesis; epoxides; regioselectivity; synthetic methods;

D O I：

10.1002/anie.200352431

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Four flavors for epoxide openings: The regioselective openings of epoxy amides obtained by asymmetric epoxidation yields all types of aryl- and alkyl-substituted hydroxy amides sometimes counter to the reactivity of the α- and β-positions.

引用

页码：317 / 320

页数：4

共 32 条

[11] ASYMMETRIC-SYNTHESIS OF BOTH ENANTIOMERS OF TOMOXETINE AND FLUOXETINE - SELECTIVE REDUCTION OF 2,3-EPOXYCINNAMYL ALCOHOL WITH RED-AL [J].

GAO, Y ;

SHARPLESS, KB .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (17) :4081-4084

[12]

Goodman S. N, 2002, ANGEW CHEM INT EDIT, V114, P4897

[13] Enantiopure β-hydroxy morpholine amides from terminal epoxides by carbonylation at 1 atm [J].

Goodman, SN ;

Jacobsen, EN .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2002, 41 (24) :4703-4705

[14] Cp2TiCl-mediated selective reduction of α,β-epoxy ketones [J].

Hardouin, C ;

Chevallier, F ;

Rousseau, B ;

Doris, E .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (03) :1046-1048

[15] A practical asymmetric synthesis of (R)-fluoxetine and its major metabolite (R)-norfluoxetine [J].

Hilborn, JW ;

Lu, ZH ;

Jurgens, AR ;

Fang, QK ;

Byers, P ;

Wald, SA ;

Senanayake, CH .

TETRAHEDRON LETTERS, 2001, 42 (51) :8919-8921

[16] A first theoretical study on the origin of the metal-mediated regioselective opening of 2,3-epoxy alcohols [J].

Infante, I ;

Bonini, C ;

Lelj, F ;

Righi, G .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (10) :3773-3780

[17] A CONVENIENT METHOD FOR PREPARING ENANTIOMERICALLY PURE NORFLUOXETINE, FLUOXETINE AND TOMOXETINE [J].

KOENIG, TM ;

MITCHELL, D .

TETRAHEDRON LETTERS, 1994, 35 (09) :1339-1342

[18] A NEW CHEMOENZYMATIC ENANTIOSELECTIVE SYNTHESIS OF R-(-)-TOMOXETINE, (R)-FLUOXETINE AND (S)-FLUOXETINE [J].

KUMAR, A ;

NER, DH ;

DIKE, SY .

TETRAHEDRON LETTERS, 1991, 32 (16) :1901-1904

[19] Epoxy ketones as versatile building blocks in organic synthesis [J].

Lauret, C .

TETRAHEDRON-ASYMMETRY, 2001, 12 (17) :2359-2383

[20] SYNTHESIS OF SACCHARIDES AND RELATED POLYHYDROXYLATED NATURAL-PRODUCTS .2. SIMPLE DEOXYALDITOLS [J].

MA, P ;

MARTIN, VS ;

MASAMUNE, S ;

SHARPLESS, KB ;

VITI, SM .

JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (07) :1378-1380

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