Synthesis of chiral bicyclo[2.2.2]oct-5-en-2-ones via an intramolecular alkylation reaction

被引：28

作者：

Srikrishna, A

Sharma, GVR

Danieldoss, S

Hemamalini, P

机构：

[1] Department of Organic Chemistry, Indian Institute of Science

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1996年 / 11期

关键词：

D O I：

10.1039/p19960001305

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Generation of the thermodynamic dienolate of 9-bromocarvone derivatives 5, 7 and 11 furnished the chiral bicycle[2.2.2] octenones 6, 8 and 9 and 12 and 13 containing a bridgehead methyl group via an intramolecular alkylation reaction. In an analogous manner intramolecular alkylation reaction of the bromo enones 15a-e, obtained from carvone 2 by 1,3-alkylative enone transposition (-->14) followed by a regiospecific bromoetherification reaction, furnished the bicyclo[2.2.2]oct-5-en-2-ones 16a-e and 17a-e.

引用

页码：1305 / 1311

页数：7

共 50 条

[1] Photochemical Rearrangements of Chiral Bicyclo[2.2.2]oct-5-en-2-ones
Srikrishna, A.
Danieldoss, S.
Synthetic Communications, 27 (04):
[2] REGIOSPECIFIC SYNTHESIS OF CHIRAL BICYCLO[2.2.2]OCT-5-EN-2-ONES FROM S-CARVONE
SRIKRISHNA, A
HEMAMALINI, P
INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1990, 29 (03): : 201 - 202
[3] BICYCLO[2.2.2]OCT-5-EN-2-ONES AS INTERMEDIATES IN THE SYNTHESIS OF NATURAL-PRODUCTS
YATES, P
BURNELL, DJ
MACAS, TS
STEVENS, KE
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1983, 185 (MAR): : 43 - ORGN
[4] Synthesis of bicyclo[4.1.0]hept-2-enes (trinorcarenes) by photochemical reaction of bicyclo[2.2.2]oct-5-en-2-ones
Katayama, S
Hiramatsu, H
Aoe, K
Yamauchi, M
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (04): : 561 - 576
[5] SYNTHESIS IN BICYCLO[2.2.2]OCTANE SERIES .2. ALKYL-SUBSTITUTED BICYCLO[2.2.2]OCT-5-EN-2-ONES
GERIBALDI, S
TORRI, G
AZZARO, M
BULLETIN DE LA SOCIETE CHIMIQUE DE FRANCE PARTIE II-CHIMIE MOLECULAIRE ORGANIQUE ET BIOLOGIQUE, 1973, (9-10): : 2836 - 2838
[6] Synthesis of bicyclo[2.2.2]oct-5-en-2-ones via a tandem intermolecular Michael addition intramolecular aldol process (a bridged Robinson annulation)
Jung, ME
Maderna, A
TETRAHEDRON LETTERS, 2005, 46 (30) : 5057 - 5061
[7] Chiral synthons from carvone .24. Photochemical rearrangements of chiral bicyclo[2.2.2]oct-5-en-2-ones
Srikrishna, A
Danieldoss, S
SYNTHETIC COMMUNICATIONS, 1997, 27 (04) : 655 - 661
[8] SYNTHESIS OF SOME BICYCLO[2.2.2]OCT-5-EN-2-ONES AND BICYCLO[2.2.2]OCTAN-2-ONES - REARRANGEMENTS ACCOMPANYING OXIDATIVE DECARBOXYLATION WITH LEAD-TETRAACETATE
YATES, P
LANGFORD, GE
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1981, 59 (02): : 344 - 355
[9] Carbohydrate-Templated Asymmetric Diels-Alder Reactions of Masked ortho-Benzoquinones for the Synthesis of Chiral Bicyclo[2.2.2]oct-5-en-2-ones
Luo, Shun-Yuan
Jang, Yeong-Jiunn
Liu, Jing-Yuan
Chu, Chrong-Shyua
Liao, Chun-Chen
Hung, Shang-Cheng
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (42) : 8082 - 8085
[10] Formation of an exceptionally stable ketene during phototransformations of bicyclo[2.2.2]oct-5-en-2-ones having mixed chromophores
Ghosh, Asitanga
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2020, 16 : 2297 - 2303

← 1 2 3 4 5 →