Hydroboration of 1,1'-Bi(cyclopent-1-ene) and 3,3'-Biindene: Experimental and Theoretical Study

[img]PDF - Authorized users only
Language: English
310Kb
Title:Hydroboration of 1,1'-Bi(cyclopent-1-ene) and 3,3'-Biindene: Experimental and Theoretical Study
Creators:
Kvíčala, Jaroslav
Baszczyňski, Ondřej
Krupková, Alena
Stránská, Denisa
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 71, 11-12, pp. 1611-1626
Uncontrolled Keywords:X-Ray diffraction, Chiral diols, Boranes, Absolute configuration, Asymmetric hydroboration, DFT calculations, Mosher's esters, Dienes

Abstract

Hydroboration of bi(cyclopent-1-ene) (<strong>1</strong>) or 3,3'-biindene (<strong>2</strong>) with borane, thexylborane or (-)-isopinocampheylborane afforded, regardless of reaction conditions, <i>meso</i>-isomers of polycyclic 1,4-diols <strong>3a</strong>, <strong>4a</strong> as the main products. No reaction was observed with 9-BBN. The structure of the major product <strong>4a</strong>, as well as of the minor racemic product <strong>4b</strong> was assigned based on <sup>1</sup>H NMR spectra of the corresponding Mosher's diesters <strong>5a</strong>-<strong>5c</strong>. Finally, the stereochemistry of the product <strong>4a</strong> was confirmed by a single-crystal X-ray analysis of the corresponding dimesylate <strong>6</strong>. To elucidate preferential formation of the <i>meso</i>-isomers, complexes of monohydroborated intermediate with borane were studied theoretically by DFT methods. <p>

Title:Hydroboration of 1,1'-Bi(cyclopent-1-ene) and 3,3'-Biindene: Experimental and Theoretical Study
Creators:
Kvíčala, Jaroslav
Baszczyňski, Ondřej
Krupková, Alena
Stránská, Denisa
Uncontrolled Keywords:X-Ray diffraction, Chiral diols, Boranes, Absolute configuration, Asymmetric hydroboration, DFT calculations, Mosher's esters, Dienes
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:71
Number:11-12
Page Range:pp. 1611-1626
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc20061611UNSPECIFIED
ID Code:2565
Item Type:Article
Deposited On:06 Feb 2009 17:19
Last Modified:06 Feb 2009 16:19

Citation

Kvíčala, Jaroslav; Baszczyňski, Ondřej; Krupková, Alena; Stránská, Denisa (2006) Hydroboration of 1,1'-Bi(cyclopent-1-ene) and 3,3'-Biindene: Experimental and Theoretical Study. Collection of Czechoslovak Chemical Communications, 71 (11-12). pp. 1611-1626. ISSN 0010-0765

Repository Staff Only: item control page