Diastereoselective Synthesis of 7,8-Carvone Epoxides

被引：4

作者：

Pombal, Sofia ^{[1
]}

Tobal, Ignacio E. ^{[2
]}

Roncero, Alejandro M. ^{[2
]}

Rodilla, Jesus M. ^{[1
]}

Garrido, Narciso M. ^{[2
]}

Sanz, Francisca ^{[3
]}

Esteban, Alberto ^{[2
]}

Tostado, Jaime ^{[2
]}

Moro, Rosalina F. ^{[2
]}

Jose Sexmero, Maria ^{[2
]}

Jambrina, Pablo G. ^{[4
]}

Diez, David ^{[2
]}

机构：

[1] Univ Beira Interior, Fac Ciencias, FibEnTech Mat Fibrosos & Tecnol Ambientais, Dept Quim, Rua Marques de Avila e Bolama, P-6201001 Covilha, Portugal

[2] Univ Salamanca, Dept Quim Organ, Fac Ciencias Quim, Plaza Caidos 1-5, E-37008 Salamanca, Spain

[3] Univ Salamanca, Serv Difracc Rayos X, Nucleus, Plaza Caidos 1-5, E-37008 Salamanca, Spain

[4] Univ Autonoma Madrid, Fac Ciencias, Dept Quim Fis Aplicada, Ciudad Univ Cantoblanco, E-28049 Madrid, Spain

来源：

CATALYSTS | 2018年 / 8卷 / 06期

关键词：

organocatalysis; aminocatalysis; proline; carvone; epoxidation; epoxide; C-H; EPOXIDATION; CARVONE; ALKENES; OLEFINS; OXIDATION; EFFICIENT; ORGANOCATALYSIS; DERIVATIVES; ENANTIOPURE;

D O I：

10.3390/catal8060250

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

The synthesis of the two 7,8-epoxides of carvone has been attained using organocatalysis in a two-step synthetic route through a bromoester intermediate. Among the different reaction conditions tested for the bromination reaction, moderate yields and diastereoselection are achieved using proline, quinidine, and diphenylprolinol, yielding the corresponding bromoesters that were transformed separately into their epoxides, obtaining the enantiopure products.

引用

页数：12

共 50 条

[21] SYNTHESIS OF 7,8-DIOXYGENATED ISOFLAVANONES
JAIN, AC
PRASAD, AK
INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1987, 26 (12): : 1143 - 1147
[22] DIASTEREOSELECTIVE REACTIONS OF ESTER ENOLATES WITH EPOXIDES
STURM, TJ
MAROLEWSKI, AE
REZENKA, DS
TAYLOR, SK
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (09): : 2039 - 2040
[23] Highly diastereoselective synthesis of Threo or Erythro aminoalkyl epoxides from α-amino acids
J Org Chem, 21 (6696):
[24] ELECTROPHILIC QUINODIMETHANES - SYNTHESIS AND POLYMERIZATION OF 7,8-DIALKOXYCARBONYL-7,8-DICYANOQUINODIMETHANES
HALL, HK
CRAMER, RJ
MULVANEY, JE
POLYMER BULLETIN, 1982, 7 (04) : 165 - 172
[25] BINDING TO MOUSE SKIN DNA OF BENZO[A]PYRENE, ITS 7,8-DIOL AND 7,8-DIOL-9,10-EPOXIDES IN RELATION TO THE TUMORIGENICITY OF THESE COMPOUNDS
BROOKES, P
CANCER LETTERS, 1979, 6 (4-5) : 285 - 289
[26] SYNTHESIS OF (/)- AND (-)-BENZO[A]PYRENE 7,8-OXIDE
BOYD, DR
GADAGINAMATH, GS
HAMILTON, R
YAGI, H
JERINA, DM
TETRAHEDRON LETTERS, 1978, (28) : 2487 - 2490
[27] A novel and facile synthesis of 7,8-diacylcoumarins
Kotali, Antigoni
Lafazanis, Ioannis S.
Harris, Philip A.
TETRAHEDRON LETTERS, 2007, 48 (40) : 7181 - 7183
[28] SYNTHESIS OF 7-ETHOXYCARBONYL-7,8-DEHYDRORUTECARPINE
RODRIGUES, JAR
MORETTO, AL
JOURNAL OF CHEMICAL RESEARCH-S, 1993, (01): : 24 - 25
[29] HALOGENATED TERPENOIDS .7. CARVONE TETRABROMIDES AND CARVONE TETRACHLORIDES
CARMAN, RM
VENZKE, BN
AUSTRALIAN JOURNAL OF CHEMISTRY, 1973, 26 (06) : 1283 - 1296
[30] DIASTEREOSELECTIVE SYN OR ANTI OPENING OF PROPARGYLIC EPOXIDES - SYNTHESIS OF ALPHA-ALLENIC ALCOHOLS
ALEXAKIS, A
MAREK, I
MANGENEY, P
NORMANT, JF
TETRAHEDRON, 1991, 47 (09) : 1677 - 1696

← 1 2 3 4 5 →