High-speed microwave-promoted Mitsunobu inversions. Application toward the deracemization of sulcatol

被引：45

作者：

Steinreiber, A ^{[1
]}

Stadler, A ^{[1
]}

Mayer, SF ^{[1
]}

Faber, K ^{[1
]}

Kappe, CO ^{[1
]}

机构：

[1] Karl Franzens Univ Graz, Inst Chem Organ & Bioorgan Chem, A-8010 Graz, Austria

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 36期

基金：

奥地利科学基金会;

关键词：

D O I：

10.1016/S0040-4039(01)01248-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An enantioconvergent synthesis of the aggregation pheromones (R)- and (S)-suleatol (6-methyl-5-hepten-2-ol) is described. Key steps in the deracemization strategy are sequential combinations of enzymatic resolutions and Mitsunobu inversions. Racemization-free Mitsunobu transformations have been carried out within 5 min by microwave irradiation, providing the desired sulcatyl acetates with clean inversion of chirality. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：6283 / 6286

页数：4

共 30 条

[11]

Hughes D.L., 1992, ORG REACT, V42, P335, DOI DOI 10.1002/0471264180.OR042.02

[12] Progress in the Mitsunobu reaction. A review [J].

Hughes, DL .

ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1996, 28 (02) :127-164

[13]

KAISER NFK, 2000, ANGEW CHEM, V112, P3742

[14] A RULE TO PREDICT WHICH ENANTIOMER OF A SECONDARY ALCOHOL REACTS FASTER IN REACTIONS CATALYZED BY CHOLESTEROL ESTERASE, LIPASE FROM PSEUDOMONAS-CEPACIA, AND LIPASE FROM CANDIDA-RUGOSA [J].

KAZLAUSKAS, RJ ;

WEISSFLOCH, ANE ;

RAPPAPORT, AT ;

CUCCIA, LA .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (08) :2656-2665

[15] Factors influencing enantioselectivity of lipase-catalyzed hydrolysis [J].

Kinoshita, M ;

Ohno, A .

TETRAHEDRON, 1996, 52 (15) :5397-5406

[16] Microwave irradiation: more than just a method for accelerating reactions [J].

Langa, F ;

DelaCruz, P ;

DelaHoz, A ;

DiazOrtiz, A ;

DiezBarra, E .

CONTEMPORARY ORGANIC SYNTHESIS, 1997, 4 (05) :373-386

[17] Microwave-assisted high-speed chemistry: a new technique in drug discovery [J].

Larhed, M ;

Hallberg, A .

DRUG DISCOVERY TODAY, 2001, 6 (08) :406-416

[18] BIOCATALYTIC-BASED SYNTHESIS OF OPTICALLY PURE (C-6)-FUNCTIONALIZED 1-(TERT-BUTYLDIMETHYLSILYLOXY) 2-METHYL-(E)-2-HEPTENES [J].

LIANG, S ;

PAQUETTE, LA .

TETRAHEDRON-ASYMMETRY, 1990, 1 (07) :445-452

[19] New solvent free organic synthesis using focused microwaves [J].

Loupy, A ;

Petit, A ;

Hamelin, J ;

Texier-Boullet, F ;

Jacquault, P ;

Mathé, D .

SYNTHESIS-STUTTGART, 1998, (09) :1213-1234

[20] PREPARATION OF AN OPTICALLY PURE SECONDARY ALCOHOL OF SYNTHETIC PYRETHROIDS USING MICROBIAL LIPASES [J].

MITSUDA, S ;

UMEMURA, T ;

HIROHARA, H .

APPLIED MICROBIOLOGY AND BIOTECHNOLOGY, 1988, 29 (04) :310-315

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