Cyclisation of (R)- and (S)-N-allyl-N-(1-phenylethyl) methoxycarbonylacetamide mediated by Mn(III): Preparation and structural assignment of 3-aza-2-oxobicyclo[3.1.0]hexanes

被引：29

作者：

Galeazzi, R ^{[1
]}

Geremia, S ^{[1
]}

Mobbili, G ^{[1
]}

Orena, M ^{[1
]}

机构：

[1] UNIV ANCONA,DIPARTIMENTO SCI MAT & TERRA,I-60131 ANCONA,ITALY

来源：

TETRAHEDRON-ASYMMETRY | 1996年 / 7卷 / 12期

关键词：

D O I：

10.1016/S0957-4166(96)00466-1

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

(R)- and (S)-N-allyl-N-(I-phenylethyl)methoxycarbonylacetamide, 5 and 6, underwent oxidative cyclisation mediated by Mn(III), to give easily separable diastereomeric mixtures of 3-aza-2-oxobicyclo[3.1.0]hexanes 8a,b and 9a,b, respectively, whose structures were assigned on the basis of H-1 NMR spectra and then confirmed by X-ray diffraction analysis of the derivatives 11b and 14. Copyright (C) 1996 Elsevier Science Ltd.

引用

页码：3573 / 3584

页数：12

共 38 条

[1]

ALLINGER N, 1982, ACS MONOGRAPH, V177

[2] CONFORMATIONAL-ANALYSIS .130. MM2 - HYDROCARBON FORCE-FIELD UTILIZING V1 AND V2 TORSIONAL TERMS [J].

ALLINGER, NL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (25) :8127-8134

[3] SYNTHESIS AND ANTIHERPETIC ACTIVITY OF (+/-)-9-[[(Z)-2-(HYDROXYMETHYL)CYCLOPROPYL]METHYL]GUANINE AND RELATED-COMPOUNDS [J].

ASHTON, WT ;

MEURER, LC ;

CANTONE, CL ;

FIELD, AK ;

HANNAH, J ;

KARKAS, JD ;

LIOU, R ;

PATEL, GF ;

PERRY, HC ;

WAGNER, AF ;

WALTON, E ;

TOLMAN, RL .

JOURNAL OF MEDICINAL CHEMISTRY, 1988, 31 (12) :2304-2315

[4] 3-oxa- and 3-azabicyclo[3.1.0]hexan-2-ones via tandem radical cyclization-intramolecular S(N)2 reactions [J].

Baldovini, N ;

Bertrand, MP ;

Carriere, A ;

Nouguier, R ;

Plancher, JM .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (09) :3205-3208

[5] CC-1065 AND THE DUOCARMYCINS - UNRAVELING THE KEYS TO A NEW CLASS OF NATURALLY DERIVED DNA ALKYLATING-AGENTS [J].

BOGER, DL ;

JOHNSON, DS .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1995, 92 (09) :3642-3649

[6] DESIGN, SYNTHESIS, AND EVALUATION OF DNA MINOR-GROOVE BINDING-AGENTS [J].

BOGER, DL .

PURE AND APPLIED CHEMISTRY, 1993, 65 (06) :1123-1132

[7]

BOGER DL, 1992, ADV HETEROCYCLIC NAT, V2, P1

[8] A NEW SYNTHESIS OF BOTH THE ENANTIOMERS OF 4-AMINO-3-HYDROXYBUTANOIC ACID (GABOB) AND MM2 CALCULATIONS FOR ROTAMERS OF THE INTERMEDIATE OXAZOLIDIN-2-ONES [J].

BONGINI, A ;

CARDILLO, G ;

ORENA, M ;

PORZI, G ;

SANDRI, S .

TETRAHEDRON, 1987, 43 (19) :4377-4383

[9] SYNTHESIS OF AMINOALCOHOLS VIA PERIHYDRO-1,3-OXAZIN-2-ONES AND ABSOLUTE-CONFIGURATION ASSIGNMENT THROUGH MM2 CALCULATIONS [J].

BONGINI, A ;

CARDILLO, G ;

ORENA, M ;

PORZI, G ;

SANDRI, S .

CHEMISTRY LETTERS, 1988, (01) :87-90

[10] SYNTHESIS OF CHIRAL 1,2-DIAMINES [J].

BRUNI, E ;

CARDILLO, G ;

ORENA, M ;

SANDRI, S ;

TOMASINI, C .

TETRAHEDRON LETTERS, 1989, 30 (13) :1679-1682

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