Sulfinimine mediated asymmetric synthesis of 3-substituted -1(2H)-isoquinolones: (3R,4S)-(-)-4-hydroxy-3-phenyltetrahydroisoquinoline

被引：20

作者：

Davis, FA ^{[1
]}

Andemichael, YW ^{[1
]}

机构：

[1] Temple Univ, Dept Chem, Philadelphia, PA 19122 USA

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 20期

基金：

美国国家卫生研究院;

关键词：

D O I：

10.1016/S0040-4039(98)00506-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A general approach to enantiomerically pure 3-substituted-1 (2H)-isoquinolones is illustrated by the addition of lateral lithiated amide 7 to sulfinimine 5. Isoquinolone 8 is readily transformed into (3R,4S)-(-)-4-hydroxy-3-phenyltetrahydroisoquinoline 15 via hydroxylation and reduction. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：3099 / 3102

页数：4

共 38 条

[1] REACTION OF 1,2-DIARYLETHYLAMIDES WITH ETHYL POLYPHOSPHATE (EPP) - CORRELATION OF THE VONBRAUN, RITTER AND BISCHLER-NAPIERALSKI REACTIONS
AGUIRRE, JM
ALESSO, EN
IBANEZ, AF
TOMBARI, DG
IGLESIAS, GYM
[J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 1989, 26 (01) : 25 - 27
[2] [Anonymous], ALKALOIDS
[3] Stereochemistry .87. Synthesis of chiral non-racemic 2-arylpyrrolines by a [3+2] cycloaddition route
Balasubramanian, T
Hassner, A
[J]. TETRAHEDRON LETTERS, 1996, 37 (32) : 5755 - 5758
[4] BHAKUNI DS, 1986, ALKALOIDS, V28, P95
[5] BRINGMANN G, 1993, LIEBIGS ANN CHEM, P877
[6] Bringmann G., 1995, ALKALOIDS, V46, P127
[7] SYNTHETIC STUDIES ON THE LITHIATED TOLUAMIDE-IMINE CYCLO-ADDITION ROUTE TO (+/-)-CORYDALIC ACID METHYL-ESTER
CLARK, RD
JAHANGIR
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (05) : 1174 - 1178
[8] DIASTEREOSELECTIVE ADDITION OF LITHIATED N,N-DIETHYL-ORTHO-TOLUAMIDE TO CHIRAL ISOPROPYLIDINE GLYCERALDEHYDE IMINES - ASYMMETRIC-SYNTHESIS OF 3-SUBSTITUTED 3,4-DIHYDRO-1(2H)-ISOQUINOLONES
CLARK, RD
JAHANGIR
SOUCHET, M
KERN, JR
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (14) : 930 - 931
[9] CLARK RD, 1995, ORG REACTIONS, V47, P5
[10] TOTAL SYNTHESIS OF (+/-)-CHELIDONINE
CUSHMAN, M
CHOONG, TC
VALKO, JT
KOLECK, MP
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (25) : 5067 - 5073

← 1 2 3 4 →