New chiral selenium electrophiles derived from functionalized terpenes

被引：18

作者：

Scianowski, Jacek ^{[1
]}

Rafinski, Zbigniew ^{[1
]}

Szuniewicz, Aleksandra ^{[1
]}

Wojtczak, Andrzej ^{[2
]}

机构：

[1] Nicholas Copernicus Univ, Dept Organ Chem, PL-87100 Torun, Poland

[2] Nicholas Copernicus Univ, Dept Crystallochem & Biocrystallog, PL-87100 Torun, Poland

来源：

TETRAHEDRON | 2009年 / 65卷 / 49期

关键词：

Terpenoids; Diselenides; Asymmetric synthesis; Selenenylation reaction; ASYMMETRIC ADDITION-REACTIONS; DIALKYL DISELENIDES; ORGANIC-COMPOUNDS; NITROGEN ATOM; METHOXYSELENENYLATIONS; DIETHYLZINC; CATALYSTS;

D O I：

10.1016/j.tet.2009.10.005

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A convenient method for the synthesis of optically active dialkyl diselenides derived from bicyclic terpenes functionalized with hydroxy, etheral. sulfide, and selenide groups is described. The diselenides were used for a synthesis of chiral electrophilic selenium reagents, then in the asymmetric selenenylation of styrene and selenocyclization with o-allylphenol. The influence of nonbonding selenium-heteroatom interactions in the generated organoselenium electrophiles on the stereo-selectivity of an addition reaction has been investigated. Calculations by a DFT method on a B3LYP (6-311G (d)) level, confirmed the existence of nonbonded selenium-heteroatom interactions in the investigated systems. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：10162 / 10174

页数：13

共 42 条

[1]

[Anonymous], 1999, ORGANOSELENIUM CHEM

[2] Asymmetric electrophilic methoxyselenenylations and cyclizations with 3-camphorseleno derivatives [J].

Back, TG ;

Dyck, BP ;

Nan, SQ .

TETRAHEDRON, 1999, 55 (11) :3191-3208

[3] Asymmetric cyclization of unsaturated alcohols and carboxylic acids with camphor-based selenium electrophiles [J].

Back, TG ;

Dyck, BP .

CHEMICAL COMMUNICATIONS, 1996, (22) :2567-2568

[4] Asymmetric methoxyselenenylations with camphor-based selenium electrophiles [J].

Back, TG ;

Nan, S .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (19) :3123-3124

[5] Diselenides and allyl selenides as glutathione peroxidase mimetics.: Remarkable activity of cyclic seleninates produced in situ by the oxidation of allyl ω-hydroxyalkyl selenides [J].

Back, TG ;

Moussa, Z .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (44) :13455-13460

[6] New chiral auxiliaries for highly stereoselective asymmetric methoxyselenenylations [J].

Back, TG ;

Moussa, Z .

ORGANIC LETTERS, 2000, 2 (19) :3007-3009

[7] DENSITY-FUNCTIONAL THERMOCHEMISTRY .3. THE ROLE OF EXACT EXCHANGE [J].

BECKE, AD .

JOURNAL OF CHEMICAL PHYSICS, 1993, 98 (07) :5648-5652

[8] VAN DER WAALS VOLUMES + RADII [J].

BONDI, A .

JOURNAL OF PHYSICAL CHEMISTRY, 1964, 68 (03) :441-+

[9] Synthesis of new chiral aliphatic amino diselenides and their application as catalysts for the enantioselective addition of diethylzinc to aldehydes [J].

Braga, AL ;

Paixao, MW ;

LUdtke, DS ;

Silveira, CC ;

Rodrigues, OED .

ORGANIC LETTERS, 2003, 5 (15) :2635-2638

[10] New developments with chiral electrophilic selenium reagents [J].

Browne, Danielle M. ;

Wirth, Thomas .

CURRENT ORGANIC CHEMISTRY, 2006, 10 (15) :1893-1903

← 1 2 3 4 5 →