Regio-selective reduction of the C-C double bonds in α,β-unsaturated acyl 4-substituted oxazolidin-2-ones and oxazolidine-2-thiones

被引：5

作者：

Li, Shao-Gang ^{[1
]}

Jin, Jian-Wei ^{[1
]}

Wu, Yikang ^{[1
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Bioorgan & Nat Prod Chem, Shanghai 200032, Peoples R China

来源：

TETRAHEDRON | 2012年 / 68卷 / 03期

基金：

中国国家自然科学基金;

关键词：

Reduction; Alkenes; Chiral auxiliary; Hydride; Stereochemistry; ASYMMETRIC-SYNTHESIS; CARBONYL-COMPOUNDS; CONJUGATE REDUCTION; CHIRAL AUXILIARIES; N-ACYLATION; 2-OXAZOLIDINONES; OXAZOLIDINONES; REAGENTS; LITHIUM; ACIDS;

D O I：

10.1016/j.tet.2011.11.038

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Selective saturation of the conjugated C-C double bonds in the title compounds was examined in a systematic way for the first time. Many established protocols effective for similar reduction of alpha,beta-unsaturated ketones and esters in the literature were found to be inapplicable in the present context. The most satisfactory results were finally obtained using the DIBAL-H/MeLi/Cul/HMPA/THF conditions. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：846 / 850

页数：5

共 25 条

[1] 1,2-amino alcohols and their heterocyclic derivatives as chiral auxiliaries in asymmetric synthesis [J].

Ager, DJ ;

Prakash, I ;

Schaad, DR .

CHEMICAL REVIEWS, 1996, 96 (02) :835-875

[2]

Ager DJ, 1996, SYNTHESIS-STUTTGART, P1283

[3] DCC/DMAP-mediated coupling of carboxylic acids with oxazolidinones and thiazolidinethiones [J].

Andrade, CKZ ;

Rocha, RO ;

Vercillo, OE ;

Silva, WA ;

Matos, RAF .

SYNLETT, 2003, (15) :2351-2352

[4] NEW AND EFFECTIVE REAGENTS FOR 1,4 REDUCTION OF ALPHA,BETA-UNSATURATED KETONES, LIALH-4-CUI AND ITS REACTIVE SPECIES H-2ALI [J].

ASHBY, EC ;

LIN, JJ ;

KOVAR, R .

JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (11) :1939-1943

[5] BASE-INDUCED C-5 EPIMERIZATION OF 4-METHYL-5-PHENYL OXAZOLIDINONES - CHIRAL AUXILIARIES DERIVED FROM NOREPHEDRINE AND NORPSEUDOEPHEDRINE [J].

DAVIES, SG ;

DOISNEAU, GJM .

TETRAHEDRON-ASYMMETRY, 1993, 4 (12) :2513-2516

[6] A short approach to the bicyclo[4.3.0]nonane fragment of stawamycin [J].

Dias, LC ;

Melgar, GZ ;

Jardim, LSA .

TETRAHEDRON LETTERS, 2005, 46 (26) :4427-4431

[7] Enantioselective synthesis of α-fluorinated β2-amino acids [J].

Edmonds, Michael K. ;

Graichen, Florian H. M. ;

Gardiner, James ;

Abell, Andrew D. .

ORGANIC LETTERS, 2008, 10 (05) :885-887

[8] CONJUGATE REDUCTION OF ALPHA,BETA-UNSATURATED CARBONYL-COMPOUNDS BY CATECHOLBORANE [J].

EVANS, DA ;

FU, GC .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (22) :5678-5680

[9] ASYMMETRIC-SYNTHESIS OF CALYCULIN-A .1. THE C-1-C-25 SPIROKETAL FRAGMENT [J].

EVANS, DA ;

GAGE, JR .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (07) :1958-1961

[10] ASYMMETRIC-SYNTHESIS OF THE MACROLIDE (+)-A83543A (LEPICIDIN) AGLYCON [J].

EVANS, DA ;

BLACK, WC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (06) :2260-2262

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