Preparation of enantiomerically pure cis- and trans-N-(propionyl)hexahydrobenzoxazolidin-2-ones

被引：23

作者：

deParrodi, CA

Juaristi, E

Quintero, L

ClaraSosa, A

机构：

[1] INST POLITECN NACL, CTR INVEST & ESTUDIOS AVANZADOS, DEPT QUIM, MEXICO CITY 07000, DF, MEXICO

[2] UNIV AMERICAS PUEBLA, DEPT QUIM & BIOL, CHOLULA 72820, MEXICO

[3] UNIV AUTONOMA PUEBLA, FAC CIENCIAS QUIM, CTR INVEST, PUEBLA 72570, MEXICO

来源：

TETRAHEDRON-ASYMMETRY | 1997年 / 8卷 / 07期

关键词：

D O I：

10.1016/S0957-4166(97)00064-5

中图分类号：

O61 [无机化学];

学科分类号：

070301 [无机化学]; 081704 [应用化学];

摘要：

A high-yield, five-step synthesis of novel enantiomerically pure cis- and trans-N-(propionyl)-hexahydrobenzoxazolidin-2-ones 5a-d from cyclohexene oxide and (S)-alpha-methylbenzylamine is described. The highly diastereoselective benzylation of 5b is also described. (C) 1997 Elsevier Science Ltd.

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页码：1075 / 1082

页数：8

相关论文

共 23 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]

[Anonymous], [No title captured]

[3]

Asymmetric Diels-Alder reactions employing modified camphor-derived oxazolidin-2-one chiral auxiliaries [J].

Banks, MR ;

Blake, AJ ;

Cadogan, JIG ;

Doyle, AA ;

Gosney, I ;

Hodgson, PKG ;

Thorburn, P .

TETRAHEDRON, 1996, 52 (11) :4079-4094

[4]

Synthesis and antibacterial activity of new tropone-substituted phenyloxazolidinone antibacterial agents .1. Identification of leads and importance of the tropone substitution pattern. [J].

Barbachyn, MR ;

Toops, DS ;

Ulanowicz, DA ;

Grega, KC ;

Brickner, SJ ;

Ford, CW ;

Zurenko, GE ;

Hamel, JC ;

Schaadt, RD ;

Stapert, D ;

Yagi, BH ;

Buysse, JM ;

Demyan, WF ;

Kilburn, JO ;

Glickman, SE .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1996, 6 (09) :1003-1008

[5]

New enantiomerically pure aminoalcohols from (R)-alpha-methylbenzylamine and cyclohexene oxide [J].

Barbaro, P ;

Bianchini, C ;

Sernau, V .

TETRAHEDRON-ASYMMETRY, 1996, 7 (03) :843-850

[6]

CONJUGATE ADDITION OF CHLORIDE TO ALPHA,BETA-UNSATURATED CHIRAL IMIDES PROMOTED BY BCL3-DERIVATIVES .2. [J].

CARDILLO, G ;

DIMARTINO, E ;

GENTILUCCI, L ;

TOMASINI, C ;

TOMASONI, L .

TETRAHEDRON-ASYMMETRY, 1995, 6 (08) :1957-1963

[7]

4-SUBSTITUTED-5,5-DIMETHYL OXAZOLIDIN-2-ONES AS EFFECTIVE CHIRAL AUXILIARIES FOR ENOLATE ALKYLATIONS AND MICHAEL ADDITIONS [J].

DAVIES, SG ;

SANGANEE, HJ .

TETRAHEDRON-ASYMMETRY, 1995, 6 (03) :671-674

[8]

deParrodi CA, 1996, AN QUIM, V92, P400

[9]

ASYMMETRIC DIELS-ALDER CYCLO-ADDITION REACTIONS WITH CHIRAL ALPHA, BETA-UNSATURATED N-ACYLOXAZOLIDINONES [J].

EVANS, DA ;

CHAPMAN, KT ;

BISAHA, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (04) :1238-1256

[10]

CHIRAL ENOLATE DESIGN [J].

EVANS, DA ;

TAKACS, JM ;

MCGEE, LR ;

ENNIS, MD ;

MATHRE, DJ ;

BARTROLI, J .

PURE AND APPLIED CHEMISTRY, 1981, 53 (06) :1109-1127