Stereochemistry of α-(tert-butoxycarbonylamino) hydroxylamines:: 1H NMR analysis of hydroxylamines derived from 2-pyrrolidinyl nitrones

被引：8

作者：

Merino, P ^{[1
]}

Franco, S ^{[1
]}

Gascon, JM ^{[1
]}

Merchan, FL ^{[1
]}

Tejero, T ^{[1
]}

机构：

[1] Univ Zaragoza, Fac Ciencias, ICMA, Dept Quim Organ, E-50009 Aragon, Spain

来源：

TETRAHEDRON-ASYMMETRY | 1999年 / 10卷 / 10期

关键词：

D O I：

10.1016/S0957-4166(99)00202-5

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Hydroxylamines derived from 2-pyrrolidinyl nitrones can be easily and unambiguously distinguished by H-1 NMR spectroscopy. A strong hydrogen bond which can be observed both in the solid state and solution is responsible for the preferred conformation of the title compounds. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：1861 / 1865

页数：5

共 15 条

[1]

DELLEMONACHE G, 1995, SYNTHESIS-STUTTGART, P1155

[2]

DONDONI A, 1994, CHEM COMMUN, P1731

[3] THE SYNTHESIS AND CONFIGURATIONAL STABILITY OF DIFFERENTIALLY PROTECTED BETA-HYDROXY-ALPHA-AMINO ALDEHYDES [J].

GARNER, P ;

PARK, JM .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (12) :2361-2364

[4] Chiral hydroxylamines .2. (1R,2R)-N-benzyl-N-[(3-tert-butoxycarbonyl-2,2-di-methyloxazol-4-yl) (furan-2-yl)methyl]-hydroxylamine [J].

Merino, P ;

Merchan, FL ;

Tejero, T ;

Lanaspa, A .

ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1996, 52 :2536-2538

[5] Enantiodivergent approach to D- and L-secondary N-hydroxy-α-amino acids by using N-benzyl-2,3-O-isopropylidene-D-glyceraldehyde nitrone as an effective N-hydroxyglycine cation equivalent [J].

Merino, P ;

Castillo, E ;

Franco, S ;

Merchan, FL ;

Tejero, T .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (07) :2371-2374

[6] Asymmetric synthesis of an isoxazolidine nucleoside analog of thymine polyoxin C [J].

Merino, P ;

Franco, S ;

Merchan, FL ;

Tejero, T .

TETRAHEDRON LETTERS, 1998, 39 (35) :6411-6414

[7] Modified nucleosides from nitrones: a new and efficient stereoselective approach to isoxazolidinyl thymidine derivatives [J].

Merino, P ;

Franco, S ;

Garces, N ;

Merchan, FL ;

Tejero, T .

CHEMICAL COMMUNICATIONS, 1998, (04) :493-494

[8]

Merino P, 1998, RRD SYNTH ORG CHEM, V1, P109

[9] Nucleophilic additions of Grignard reagents to N-benzyl-2,3-O-isopropylidene-D-glyceraldehyde nitrone (BIGN).: Synthesis of (2S,3R) and (2S,3S)-3-phenylisoserine. [J].

Merino, P ;

Castillo, E ;

Franco, S ;

Merchán, FL ;

Tejero, T .

TETRAHEDRON, 1998, 54 (40) :12301-12322

[10] Ready access to enantiopure 5-substituted-3-pyrrolin-2-ones from N-benzyl-2,3-O-isopropylidene-D-glyceraldehyde nitrone (BIGN) [J].

Merino, P ;

Castillo, E ;

Franco, S ;

Merchan, FL ;

Tejero, T .

TETRAHEDRON-ASYMMETRY, 1998, 9 (10) :1759-1769

← 1 2 →