Spiro[4.5]deca-2,7-diene-1,6-dione and Spiro[5.5]undeca-2,8-diene-1,7-dione. Synthesis, Reductions and Palladium-Catalyzed Allylic Substitutions

[img]PDF - Authorized users only
Language: English
82Kb
Title:Spiro[4.5]deca-2,7-diene-1,6-dione and Spiro[5.5]undeca-2,8-diene-1,7-dione. Synthesis, Reductions and Palladium-Catalyzed Allylic Substitutions
Creators:
Sirbu, Doina
Sunel, Valeriu
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 66, 10, pp. 1521-1528
Uncontrolled Keywords:Spirodecane, Spirocyclic compounds, Cyclic allyl alcohols, Spiranes, Allylic substitutions, Reductions, Spiroundecane

Abstract

Spiro[4,5]deca-2,7-diene-1,6-dione (<strong>2a</strong>) and spiro[5,5]undeca-2,8-diene-1,7-dione (<strong>2b</strong>) were prepared by a direct synthesis starting from diethyl malonate. The two-step 1,2-reductions (NaBH<sub>4</sub>/CeCl<sub>3</sub>) of the diones gave <i>cis</i>/<i>trans</i>-diols, which could be easily transformed into diacetates. Both diacetates were subjected to Pd(0)-catalyzed allylic alkylations, in which the relative stereochemistry was retained. <p>

Title:Spiro[4.5]deca-2,7-diene-1,6-dione and Spiro[5.5]undeca-2,8-diene-1,7-dione. Synthesis, Reductions and Palladium-Catalyzed Allylic Substitutions
Creators:
Sirbu, Doina
Sunel, Valeriu
Uncontrolled Keywords:Spirodecane, Spirocyclic compounds, Cyclic allyl alcohols, Spiranes, Allylic substitutions, Reductions, Spiroundecane
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:66
Number:10
Page Range:pp. 1521-1528
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc20011521UNSPECIFIED
ID Code:1875
Item Type:Article
Deposited On:06 Feb 2009 17:13
Last Modified:06 Feb 2009 16:13

Citation

Sirbu, Doina; Sunel, Valeriu (2001) Spiro[4.5]deca-2,7-diene-1,6-dione and Spiro[5.5]undeca-2,8-diene-1,7-dione. Synthesis, Reductions and Palladium-Catalyzed Allylic Substitutions. Collection of Czechoslovak Chemical Communications, 66 (10). pp. 1521-1528. ISSN 0010-0765

Repository Staff Only: item control page