DIASTEREOSELECTION IN THE LEWIS ACID-CATALYZED CYCLOADDITION REACTION OF ALPHA-ALKOXY IMINES

被引：54

作者：

MIDLAND, MM

KOOPS, RW

机构：

[1] Department of Chemistry, University of California, Riverside

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1992年 / 57卷 / 04期

关键词：

D O I：

10.1021/jo00030a023

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Lewis acid catalyzed cycloaddition reactions of alpha-benzyloxy imines (RCH(OCH2C6H5)CH = NCH2C6H5) were investigated using 1,3-dimethoxy-1-[(trimethylsilyl)oxy]-1,3-butadiene. The observed diastereoselectivity was dependent on both the Lewis acid and substrate structure. Strong Lewis acids such as diethylaluminum chloride (DEAC) exhibited moderate to good success in promoting the cycloaddition reaction. When DEAC was used as the Lewis acid, the diastereoselectivity was also dependent on the stoichiometry of the Lewis acid to the substrate. In general, the diastereoselectivity increased with increasing steric bulk of the R group.

引用

页码：1158 / 1161

页数：4

共 36 条

[1] ARJONA O, 1984, AN QUIM C-ORG BIOQ, V80, P304
[2] CHELATION IN ORGANOALUMINUM-NITROGEN CHEMISTRY
BEACHLEY, OT
RACETTE, KC
[J]. INORGANIC CHEMISTRY, 1976, 15 (09) : 2110 - 2115
[3] FALSE IMPRESSIONS FROM AL-27 NMR-SPECTROSCOPY
BENN, R
RUFINSKA, A
JANSSEN, E
LEHMKUHL, H
[J]. ORGANOMETALLICS, 1986, 5 (04) : 825 - 827
[4] AL-27-NMR SPECTROSCOPY - A PROBE FOR THREEFOLD, FOURFOLD, FIVEFOLD, AND SIXFOLD COORDINATED AL ATOMS IN ORGANO-ALUMINUM COMPOUNDS
BENN, R
RUFINSKA, A
LEHMKUHL, H
JANSSEN, E
KRUGER, C
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1983, 22 (10): : 779 - 780
[5] BRASSARD P, 1979, TETRAHEDRON LETT, V20, P4911
[6] A CONCISE TOTAL SYNTHESIS OF (+/-)-IPALBIDINE BY APPLICATION OF THE ALDIMINE-DIENE CYCLOCONDENSATION REACTION
DANISHEFSKY, SJ
VOGEL, C
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (20) : 3915 - 3916
[7] CHELATION-CONTROLLED FACIALLY SELECTIVE CYCLOCONDENSATION REACTIONS OF CHIRAL ALKOXY ALDEHYDES - SYNTHESES OF A MOUSE ANDROGEN AND OF A CARBON-LINKED DISACCHARIDE
DANISHEFSKY, SJ
PEARSON, WH
HARVEY, DF
MARING, CJ
SPRINGER, JP
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (05) : 1256 - 1268
[8] DEKIMPE N, 1984, CAN J CHEM, V62, P1812
[9] C-13 SHIELDINGS IN SYN AND ANTI ALDIMINES AND KETIMINES
FRASER, RR
BANVILLE, J
AKIYAMA, F
CHUAQUIOFFERMANNS, N
[J]. CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1981, 59 (04): : 705 - 709
[10] AN INTRAMOLECULAR IMMONIUM ION VARIATION OF THE DIELS-ALDER REACTION - SYNTHESIS OF (+/-)-DIHYDROCANNIVONINE
GRIECO, PA
LARSEN, SD
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (18) : 3553 - 3555

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