Lewis acid-promoted synthesis and reactivity of β-O-benzylhydroxylamino imides derived from D-glyceraldehyde

被引：20

作者：

Cardillo, G ^{[1
]}

Gentilucci, L ^{[1
]}

De Matteis, V ^{[1
]}

机构：

[1] Univ Bologna, Dipartimento Chim G Ciamician, I-40128 Bologna, Italy

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2002年 / 67卷 / 17期

关键词：

D O I：

10.1021/jo0259055

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

This paper describes the synthesis and use of beta-hydroxylamino imides derived from D-glyceraldehyde possessing a number of reactive sites that operate synergistically or alternatively to bring about highly regio- and diastereoselective transformations to give an optically pure aziridine-2-imide, a dihydro pyrimidine-2,4-dione, or a lactone. Both the syntheses, via the diastereoselective 1,4-conjugate addition of O-benzyl hydroxylamine to alpha,beta-unsaturated imides, and transformations can be simply tuned by choosing between different Lewis acids.

引用

页码：5957 / 5962

页数：6

共 46 条

[11] Cardillo G, 2001, EUR J ORG CHEM, V2001, P3545
[12] STEREOSELECTIVE APPROACHES TO BIOACTIVE CARBOHYDRATES AND ALKALOIDS - WITH A FOCUS ON RECENT SYNTHESES DRAWING FROM THE CHIRAL POOL
CASIRAGHI, G
ZANARDI, F
RASSU, G
SPANU, P
[J]. CHEMICAL REVIEWS, 1995, 95 (06) : 1677 - 1716
[13] Total synthesis of a thymidine 2-deoxypolyoxin C analogue
Dehoux, C
Fontaine, E
Escudier, JM
Baltas, M
Gorrichon, L
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (08) : 2601 - 2608
[14] DIASTEREOSELECTIVE CONVERSION OF L-(S)-ERYTHRULOSE TO 2-AMINO-2-DEOXY-L-ERYTHRITOL
DEQUEKER, E
COMPERNOLLE, F
TOPPET, S
HOORNAERT, G
[J]. TETRAHEDRON, 1995, 51 (20) : 5877 - 5890
[15] DUREAULT A, 1991, SYNTHESIS-STUTTGART, P150
[16] Asymmetric titanium-catalysed Michael addition of O-benzylhydroxylamine to alpha,beta-unsaturated carbonyl compounds: Synthesis of beta-amino acid precursors
Falborg, L
Jorgensen, KA
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1996, (23): : 2823 - 2826
[17] Nostophycin, a novel cyclic peptide from the toxic cyanobacterium Nostoc sp 152
Fujii, K
Sivonen, K
Kashiwagi, T
Hirayama, K
Harada, K
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (16) : 5777 - 5782
[18] GAGE JR, 1990, ORG SYNTH, V68, P83
[19] Total synthesis of (+)-polyoxin J
Ghosh, AK
Wang, Y
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (08) : 2789 - 2795
[20] Jahnisch K, 1997, LIEBIGS ANN-RECL, P757

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