CYCLOADDITIONS .53. STEREOSELECTIVE SYNTHESIS OF FUNCTIONALIZED PYRROLIDINES VIA INTRAMOLECULAR 1,3-DIPOLAR SILYL NITRONATE CYCLOADDITION

被引：33

作者：

GOTTLIEB, L ^{[1
]}

HASSNER, A ^{[1
]}

机构：

[1] BAR ILAN UNIV,DEPT CHEM,IL-52900 RAMAT GAN,ISRAEL

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1995年 / 60卷 / 12期

关键词：

D O I：

10.1021/jo00117a030

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Michael addition products of secondary allylamines to nitroalkenes were captured as the O-silyl alpha-allylaminoalkylnitronates. These undergo stereoselective intramolecular silyl nitronate-olefin 1,3-dipolar cycloaddition to provide highly functionalized pyrrolidines.

引用

收藏

页码：3759 / 3763

页数：5

相关论文

共 38 条

[1] SILYL NITRONATES IN ORGANIC-SYNTHESIS - ROUTES TO HETEROCYCLES AND CYCLOPENTANOIDS - SYNTHESIS OF ALLETHROLONE AND CALYTHRONE - ACYLATION AND CYANOHYDROXYLATION OF DOUBLE-BONDS - AN EXPLORATORY-STUDY [J].

ANDERSEN, SH ;

DAS, NB ;

JORGENSEN, RD ;

KJELDSEN, G ;

KNUDSEN, JS ;

SHARMA, SC ;

TORSSELL, KBG .

ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1982, 36 (01) :1-14

[2]

[Anonymous], 1984, 1 3 DIPOLAR CYCLOADD

[3]

ASAOKA M, 1987, TETRAHEDRON LETT, P222

[4]

BEEBE Z, 1993, J ORG CHEM, V58, P7320

[5] NUCLEOPHILIC-ADDITION TO OLEFINS .16. UNUSUAL SUBSTITUENT EFFECTS IN THE REACTION OF AMINES WITH BETA-NITROSTYRENES - SOLVENT EFFECT ON INTRINSIC RATE CONSTANTS [J].

BERNASCONI, CF ;

RENFROW, RA ;

TIA, PR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (15) :4541-4549

[6] ON THE SCOPE OF ASYMMETRIC NITRILE OXIDE CYCLOADDITIONS WITH OPPOLZERS CHIRAL SULTAM - TOTAL SYNTHESES OF (+)-HEPIALONE, (-)-(1R,3R,5S)-1,3-DIMETHYL-2,9-DIOXABICYCLO[3.3.1]NONANE, AND (-)-(1S)-7,7-DIMETHYL-6,8-DIOXABICYCLO[3.2.1]OCTANE [J].

CURRAN, DP ;

HEFFNER, TA .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (15) :4585-4595

[7] NUCLEOPHILIC ADDITIONS TO AND REDUCTIONS OF 5-FORMYL-2-ISOXAZOLINE AND 5-ACYL-2-ISOXAZOLINE (4,5-DIHYDROISOXAZOLES) - A STEREOSELECTIVE ROUTE TO BETA,GAMMA-DIHYDROXY KETONES [J].

CURRAN, DP ;

ZHANG, JC .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (11) :2613-2625

[8]

CURRAN DP, 1988, ADV CYCLOADDITION, P129

[9]

CURRAN DP, 1991, J CHEM SOC P1, P2627

[10] STEREOCHEMISTRY .76. STEREOSELECTIVITY IN INTRAMOLECULAR 1,3-DIPOLAR CYCLOADDITIONS - NITRILE OXIDES VERSUS SILYL NITRONATES [J].

DEHAEN, W ;

HASSNER, A .

TETRAHEDRON LETTERS, 1990, 31 (05) :743-746

← 1 2 3 4 →