CREATION OF CHIRALITY IN THE REACTION OF THE CHIRAL ESTER ENOLATE-IMINE CONDENSATION LEADING TO THE STEREODIVERGENT SYNTHESIS OF BETA-LACTAMS

被引：30

作者：

SHIMIZU, M ^{[1
]}

TERAMOTO, Y ^{[1
]}

FUJISAWA, T ^{[1
]}

机构：

[1] MIE UNIV, DEPT CHEM MAT, TSU, MIE 514, JAPAN

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 05期

关键词：

D O I：

10.1016/0040-4039(94)02327-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Stereocontrol at C-4 of the p-lactams possessing substituents at 3- and 4-positions in the ester enolate-imine condensation is studied using different metal enolates of the chiral esters possessing amino alcohols derived all from (+)-camphor as an auxiliary, and 4R- or 4S-beta-lactam is obtained in a highly stereoselective manner, respectively. The effects of the structure of the chiral auxiliary and the coordination ability of the heteroatoms in the ester part are also discussed.

引用

页码：729 / 732

页数：4

共 41 条

[1] Creation of chirality in the reaction of the chiral ester enolate-imine condensation leading to the stereodivergent synthesis of QQ -lactams
Shimizu, M.
Teramoto, Y.
Fujisawa, T.
Tetrahedron Letters, 36 (05):
[2] CREATION OF CHIRALITY IN THE REACTION OF THE CHIRAL ESTER ENOLATE-IMINE CONDENSATION LEADING TO THE STEREODIVERGENT SYNTHESIS OF BETA-LACTAMS (VOL 36, PG 729, 1995)
SHIMIZU, M
TERAMOTO, Y
FUJISAWA, T
TETRAHEDRON LETTERS, 1995, 36 (25) : 4324 - 4324
[3] ASYMMETRIC-SYNTHESIS OF BETA-LACTAMS BY CHIRAL ESTER ENOLATE - IMINE CONDENSATION
OJIMA, I
HABUS, I
SILVESTRI, KC
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1990, 199 : 10 - ORGN
[4] ASYMMETRIC-SYNTHESIS OF BETA-LACTAMS BY CHIRAL ESTER ENOLATE - IMINE CONDENSATION
OJIMA, I
HABUS, I
TETRAHEDRON LETTERS, 1990, 31 (30) : 4289 - 4292
[5] DIASTEREOCONTROL VIA COSOLVENTS IN THE ZINC ESTER ENOLATE-IMINE CONDENSATION ROUTE TO BETA-LACTAMS
VANMAANEN, HL
KLEIJN, H
JASTRZEBSKI, JTBH
VANKOTEN, G
BULLETIN DE LA SOCIETE CHIMIQUE DE FRANCE, 1995, 132 (01): : 86 - 94
[6] THE ESTER ENOLATE IMINE CONDENSATION ROUTE TO BETA-LACTAMS
HART, DJ
HA, DC
CHEMICAL REVIEWS, 1989, 89 (07) : 1447 - 1465
[7] DIASTEREOFACE-DISCRIMINATION REACTION OF LITHIUM OR TITANIUM ESTER ENOLATES WITH A CHIRAL IMINE LEADING TO STEREODIVERGENT SYNTHESIS OF BETA-LACTAMS
FUJISAWA, T
UKAJI, Y
NORO, T
DATE, K
SHIMIZU, M
TETRAHEDRON, 1992, 48 (27) : 5629 - 5638
[8] ESTER ENOLATE-IMINE CONDENSATION TO BETA LACTAM: MECHANISM OF THE REACTION
Yadav, Ram Naresh
Banik, Bimal Krishna
HETEROCYCLIC LETTERS, 2022, 12 (04): : 715 - 718
[9] Theoretical study of ester enolate-imine condensation route to β-lactams
Del Río, E
López, R
Menéndez, MI
Sordo, TL
Ruiz-López, MF
JOURNAL OF COMPUTATIONAL CHEMISTRY, 1998, 19 (16) : 1826 - 1833
[10] Solid-phase synthesis of β-lactams via the ester enolate-imine condensation route
Schunk, S
Enders, D
ORGANIC LETTERS, 2000, 2 (07) : 907 - 910

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