Stereoselective synthesis of novel 4,5-epoxy-1,2-oxazin-6-ones and α,β-epoxy-γ-amino acids from β-lithiated oxazolinyloxiranes and nitrones

被引：26

作者：

Capriati, Vito

Degennaro, Leonardo

Florio, Saverio

Luisi, Renzo

Punzi, Pasqualina

机构：

[1] Univ Bari, Dipartimento Farm Chim, CNR, I-70125 Bari, Italy

[2] ICCOM, Sez Bari, I-70125 Bari, Italy

来源：

ORGANIC LETTERS | 2006年 / 8卷 / 21期

关键词：

D O I：

10.1021/ol0618609

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A stereoselective synthesis of 9,10-epoxy-1,6-dioxa-4,7-diazaspiro[4,5] decanes has been developed on the basis of the addition of beta-lithiated oxazolinyloxiranes to nitrones. Conversion of these spirocyclic derivatives into 4,5-epoxy-1,2-oxazin-6-ones and successively into alpha,beta-epoxy-amino gamma- acids, alpha-hydroxy-gamma-amino acids, and gamma-butyrolactams is described.

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页码：4803 / 4806

页数：4

相关论文

共 20 条

[1] α-γ hybrid peptides that contain the conformationally constrained gabapentin residue:: Characterization of mimetics of chain reversals [J].

Aravinda, S ;

Ananda, K ;

Shamala, N ;

Balaram, P .

CHEMISTRY-A EUROPEAN JOURNAL, 2003, 9 (19) :4789-4795

[2] α-lithiated aryloxiranes:: Useful reactive intermediates [J].

Capriati, V ;

Florio, S ;

Luisi, R .

SYNLETT, 2005, (09) :1359-1369

[3]

Capriati V, 2002, EUR J ORG CHEM, V2002, P2961, DOI 10.1002/1099-0690(200209)2002:17<2961::AID-EJOC2961>3.0.CO

[4]

2-F

[5] Stereospecific β-lithiation of oxazolinyloxiranes:: Synthesis of α,β-epoxy-γ-butyrolactones [J].

Capriati, V ;

Degennaro, L ;

Favia, R ;

Florio, S ;

Luisi, R .

ORGANIC LETTERS, 2002, 4 (09) :1551-1554

[6] β-peptides:: From structure to function [J].

Cheng, RP ;

Gellman, SH ;

DeGrado, WF .

CHEMICAL REVIEWS, 2001, 101 (10) :3219-3232

[7] Pyrrolidinone-fused cyclohexenones by regioselective dearomatising anionic cyclisation of 2-, 3- or 4-methoxybenzamides [J].

Clayden, J ;

Tchabanenko, K ;

Yasin, SA ;

Turnbull, MD .

SYNLETT, 2001, (02) :302-304

[8] Dearomatizing anionic cyclization of substituted N-cumyl-N-benzylbenzamides on treatment with LDA:: Synthesis of partially saturated substituted isoindolones [J].

Clayden, J ;

Menet, CJ ;

Mansfield, DJ .

ORGANIC LETTERS, 2000, 2 (26) :4229-4232

[9] First stereocontrolled synthesis of (S)-cleonin and related cyclopropyl-substituted amino acids [J].

Esposito, A ;

Piras, PP ;

Ramazzotti, D ;

Taddel, M .

ORGANIC LETTERS, 2001, 3 (21) :3273-3275

[10] Synthesis and applications of β-aminocarboxylic acids containing a cyclopropane ring [J].

Gnad, F ;

Reiser, O .

CHEMICAL REVIEWS, 2003, 103 (04) :1603-1623