SELF-REPRODUCTION OF CHIRALITY - ASYMMETRIC-SYNTHESIS OF BETA-ARYL-BETA-AMINO ACIDS FROM ENANTIOMERICALLY PURE DIHYDROPYRIMIDINONES

被引：65

作者：

KONOPELSKI, JP

CHU, KS

NEGRETE, GR

机构：

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1991年 / 56卷 / 04期

关键词：

D O I：

10.1021/jo00004a005

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Enantiomerically pure dihydropyrimidinone 1 reacts with aryl iodides in the presence of catalytic amounts of Pd(OAc)2 and added phosphine to afford dihydropyrimidinone 4, in which a formal conjugate addition of the aryl group to the alpha,beta-unsaturated system has occurred. Application of this methodology to the synthesis of a protected version of the tripeptide portion of the natural product jasplakinolide is presented.

引用

页码：1355 / 1357

页数：3

共 58 条

[1] A GENERAL PROCEDURE FOR THE SYNTHESIS OF ISOXAZOLIDIN-5-ONES
BALDWIN, JE
HARWOOD, LM
LOMBARD, MJ
[J]. TETRAHEDRON, 1984, 40 (21) : 4363 - 4370
[2] ASYMMETRIC-SYNTHESIS WITH CHIRAL HYDROXYLAMINES - SYNTHESIS OF OPTICALLY PURE 4-SUBSTITUTED AZETIDINONES
BALDWIN, SW
AUBE, J
[J]. TETRAHEDRON LETTERS, 1987, 28 (02) : 179 - 182
[3] JASPAMIDE FROM THE MARINE SPONGE JASPIS-JOHNSTONI
BRAEKMAN, JC
DALOZE, D
MOUSSIAUX, B
RICCIO, R
[J]. JOURNAL OF NATURAL PRODUCTS, 1987, 50 (05): : 994 - 995
[4] PALLADIUM-CATALYZED CONJUGATE ADDITION TYPE REACTION OF ARYL IODIDES WITH ALPHA,BETA-UNSATURATED KETONES
CACCHI, S
ARCADI, A
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (23) : 4236 - 4240
[5] CHIBA T, 1987, CHEM PHARM BULL, V35, P4672
[6] JASPLAKINOLIDE, A CYCLODEPSIPEPTIDE FROM THE MARINE SPONGE, JASPIS SP
CREWS, P
MANES, LV
BOEHLER, M
[J]. TETRAHEDRON LETTERS, 1986, 27 (25) : 2797 - 2800
[7] ENANTIOSELECTIVE SYNTHESIS OF BETA-AMINO ESTERS THROUGH HIGH-PRESSURE-INDUCED ADDITION OF AMINES TO ALPHA,BETA-ETHYLENIC ESTERS
DANGELO, J
MADDALUNO, J
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (25) : 8112 - 8114
[8] THE ASYMMETRIC-SYNTHESIS OF BETA-LACTAMS - STEREOCONTROLLED ASYMMETRIC TANDEM MICHAEL ADDITIONS AND ALKYLATIONS OF ALPHA,BETA-UNSATURATED ACYL LIGANDS BOUND TO THE CHIRAL AUXILIARY [BETA-C5H5)FE(CO)(PPH3)]
DAVIES, SG
DORDORHEDGECOCK, IM
SUTTON, KH
WALKER, JC
[J]. TETRAHEDRON LETTERS, 1986, 27 (32) : 3787 - 3790
[9] DREY CNC, 1985, CHEM BIOCH AMINO ACI, P25
[10] ASYMMETRIC-SYNTHESIS OF 2-AMINO-1,4-DIOLS
FERINGA, BL
DELANGE, B
[J]. TETRAHEDRON LETTERS, 1988, 29 (11) : 1303 - 1306

← 1 2 3 4 5 6 →