STEREOSELECTIVE RADICAL ADDITIONS USING CHIRAL 1,3-DIOXOLANONES DERIVED FROM LACTIC AND MALIC-ACID

被引：7

作者：

KNEER, G

MATTAY, J

HEIDBREDER, A

RAABE, G

KREBS, B

LAGE, M

机构：

[1] UNIV MUNSTER,INST ORGAN CHEM,D-48149 MUNSTER,GERMANY

[2] RHEIN WESTFAL TH AACHEN,INST ORGAN CHEM,W-5100 AACHEN,GERMANY

[3] UNIV MUNSTER,INST ANORGAN CHEM,W-4400 MUNSTER,GERMANY

来源：

JOURNAL FUR PRAKTISCHE CHEMIE-CHEMIKER-ZEITUNG | 1995年 / 337卷 / 02期

关键词：

D O I：

10.1002/prac.19953370126

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

The hydrogen abstraction of radical intermediates yielded by radical addition to the methylene compound 6, shows excellent facial selectivity. Conformational analyses of the radical intermediates were carried out by quantum chemical calculations and explain these results. The chiral radicals 7 and 8, yielded from the chiral bromides 3 and 4, lead with ethyl acrylate to the adducts 28 and 29 with more 96 % de. The adduct 28 was converted to the optically active gamma-valerolactone 30. The structures of the bromides 3, 4 and 31 as well as the radical adducts 19a, 24 and 25 have been verified by X-ray diffraction analysis.

引用

页码：113 / 124

页数：12

共 29 条

[11] HOMOCHIRAL 2,4-DISUBSTITUTED 1,3-DIOXANES FROM (S)-(-)-MALIC ACID - STEREOSELECTIVE SYNTHESIS AND INVESTIGATION OF THE NMDA RECEPTOR AFFINITY OF ALL 4 STEREOISOMERS
WUNSCH, B
DIEKMANN, H
HOFNER, G
LIEBIGS ANNALEN DER CHEMIE, 1993, (12): : 1273 - 1278
[12] Isotactic degradable polyesters derived from O-carboxyanhydrides of L-lactic and L-malic acid using a single organocatalyst/initiator system
Bexis, Panagiotis
De Winter, Julien
Coulembier, Olivier
Dove, Andrew P.
EUROPEAN POLYMER JOURNAL, 2017, 95 : 660 - 670
[13] A simple stereoselective synthesis of enantiopure 2-substituted pyrrolidines and piperidines from chiral (R)-phenylglycinol-derived bicyclic 1,3-oxazolidines
Andrés, JM
Herráiz-Sierra, I
Pedrosa, R
Pérez-Encabo, A
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2000, 2000 (09) : 1719 - 1726
[14] Chiral 1,3-aminosquaramides derived from cis-2-benzamidocyclohexanecarboxylic acid as organocatalysts for asymmetric Michael addition reactions
Kodama, Koichi
Maruyama, Kazuhisa
Hirose, Takuji
TETRAHEDRON, 2022, 112
[15] Stereoselective borane reduction of acetophenone using 1,3,2-oxazaborolidine derived from (R)-4-(diphenylhydroxymethyl)-1,3-thiazolidine
Calmes, M
Escale, F
SYNTHETIC COMMUNICATIONS, 1999, 29 (08) : 1341 - 1347
[16] Double stereodifferentiating aldol reactions based on chiral ketones derived from lactic acid:: Synthesis of C1-C6 fragment of erythronolides
Solsona, JG
Nebot, J
Romea, P
Urpí, FL
SYNLETT, 2004, (12) : 2127 - 2130
[17] ASYMMETRIC 1,3-DIPOLAR CYCLOADDITION OF NITRILE OXIDES TO NEW CHIRAL ACRYLAMIDES DERIVED FROM (S)-INDOLINE-2-CARBOXYLIC ACID
KIM, YH
KIM, SH
PARK, DH
TETRAHEDRON LETTERS, 1993, 34 (38) : 6063 - 6066
[18] Synthesis of Chiral 1,3-Diamines Derived from cis-2-Benzamidocyclohexanecarboxylic Acid and Their Application in the Cu-Catalyzed Enantioselective Henry Reaction
Kodama, Koichi
Sugawara, Kazuyuki
Hirose, Takuji
CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (48) : 13584 - 13592
[19] ENANTIOSELECTIVE SYNTHESES OF ALDOLS AND HOMOALLYLIC ALCOHOLS FROM 1,3-DIOXOLAN-4-ONES USING MANDELIC-ACID AS CHIRAL AUXILIARY
MASHRAQUI, SH
KELLOGG, RM
JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (13) : 2513 - 2516
[20] FACTORS CONTROLLING THE ENANTIOSELECTIVE ADMISSION OF CHALCONE USING CHIRAL CUPRATES .1. CHIRAL AUXILIARIES DERIVED FROM L-TARTARIC ACID AND L-PROLINE
LEYENDECKER, F
JESSER, F
LAUCHER, D
RUHLAND, B
NOUVEAU JOURNAL DE CHIMIE-NEW JOURNAL OF CHEMISTRY, 1985, 9 (01): : 7 - 12

← 1 2 3 →