SYNTHESIS OF SPIRO[4.4]NONANE-1,6-DIOLS VIA THE HYDROGENATION OF SPIRO[4.4]NONANE-1,6-DIONE - THE PROFOUND EFFECT OF HYDROGENATING AGENTS

Authors
CHAN ASC LIN CC SUN J HU WH PAN WD MI AQ JIANG YZ HUANG TM YANG TK CHEN JH WANG Y LEE GH
Citation
Asc. Chan et al., SYNTHESIS OF SPIRO[4.4]NONANE-1,6-DIOLS VIA THE HYDROGENATION OF SPIRO[4.4]NONANE-1,6-DIONE - THE PROFOUND EFFECT OF HYDROGENATING AGENTS, Tetrahedron : asymmetry, 6(12), 1995, pp. 2953-2959
Citations number
13
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
6
Issue
12
Year of publication
1995
Pages
2953 - 2959
Database
ISI
SICI code
0957-4166(1995)6:12<2953:SOSVTH>2.0.ZU;2-J
Abstract
The synthesis of spiro[4.4]nonane-1,6-diols via the catalytic as well as stoichiometric hydrogenation of spiro[4.4]nonane-1,6-dione was stud ied. Profound effects of the hydrogenation catalysts and reagents on t he stereoselectivity of the products were observed. The choice of solv ent also was found to have a significant influence on the product sele ctivity. The opening of a spiro-ring in the starting material was iden tified as a major side reaction in alcohol solvents. The absolute conf iguration of the trans,trans-diol was unambiguously determined by Xray crystallography.