HIGHLY DIASTEREOSELECTIVE ALKYLATION OF 6-METHYLPERIHYDROPYRIMIDIN-4-ONES DIRECTED TOWARDS THE SYNTHESIS OF ALPHA-SUBSTITUTED BETA-AMINO ACIDS

被引：20

作者：

AMOROSO, R ^{[1
]}

CARDILLO, G ^{[1
]}

TOMASINI, C ^{[1
]}

机构：

[1] UNIV BOLOGNA,DIPARTIMENTO CHIM G CIAMICIAN,CTR STUDIO FIS MACROMOL,VIA SELMI 2,I-40126 BOLOGNA,ITALY

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 19期

关键词：

CYCLIC CHIRAL AMIDALS; DIASTEREOSELECTIVE ALKYLATION; ALKYLATION OF (1'S; 6R)-6-METHYLPERIHYDROPYRIMIDIN-4-ONE; 6S)-6-METHYLPERIHYDROPYRIMIDIN-4-ONE; ALPHA-SUBSTITUTED BETA-AMINO ACIDS;

D O I：

10.1016/S0040-4039(00)79067-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The highly diastereoselective alkylation of 6-methylperihydropyrimidin-4-ones 1 and 2 has been reported. The corresponding lithium enolates have been alkylated under a variety of conditions with good trans selectivity and all the reaction products have been easily separated and characterised.

引用

页码：2725 / 2728

页数：4

共 38 条

[1] SYNTHESIS OF L AND D ALPHA-AMINO-ACIDS FROM CHIRAL AMIDALS
AMOROSO, R
CARDILLO, G
TOMASINI, C
[J]. TETRAHEDRON LETTERS, 1990, 31 (44) : 6413 - 6416
[2] 1,3-ASYMMETRIC INDUCTION - HIGHLY ENANTIOSELECTIVE SYNTHESIS OF ALPHA-AMINO-ACIDS VIA 2,5-TRANS DISUBSTITUTED IMIDAZOLIDIN-4-ONES
AMOROSO, R
CARDILLO, G
TOMASINI, C
[J]. TETRAHEDRON LETTERS, 1991, 32 (17) : 1971 - 1974
[3] AMOROSO R, 1992, J ORG CHEM
[4] AMOROSO R, 1992, HETEROCYCLES
[5] REACTION OF ACYLAMINO ACIDS WITH PARAFORMALDEHYDE
BENISHAI, D
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1957, 79 (21) : 5736 - 5738
[6] KINETIC RESOLUTION IN THE DIRECTED HYDROGENATION OF N-SUBSTITUTED ALPHA-(AMINOALKYL) ACRYLATES, PRECURSORS OF OPTICALLY-ACTIVE BETA-AMINO ACIDS
BROWN, JM
JAMES, AP
PRIOR, LM
[J]. TETRAHEDRON LETTERS, 1987, 28 (19) : 2179 - 2182
[7] CAINELLI G, 1987, TETRAHEDRON LETT, V8, P3593
[8] 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
[9] 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
[10] ASSIGNMENT OF THE ABSOLUTE-CONFIGURATION TO WINTERSTEIN ACID, R-3-DIMETHYLAMINO-3-PHENYL PROPIONIC-ACID, BY THE ASYMMETRIC-SYNTHESIS OF HOMOCHIRAL (S)-(+)-ETHYL 3-DIMETHYLAMINO-3-PHENYL PROPIONATE
DAVIES, SG
DUPONT, J
EASTON, RJC
[J]. TETRAHEDRON-ASYMMETRY, 1990, 1 (05) : 279 - 280

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