Dispiroketals in synthesis. Part 24. Preparation and use of chiral 2,2 '-bis(triisopropylsilyloxymethyl)bi(dihydropyran)s as new protecting and resolving agents for 1,2-diols

Authors
Laine, D Fujita, M Ley, SV
Citation
D. Laine et al., Dispiroketals in synthesis. Part 24. Preparation and use of chiral 2,2 '-bis(triisopropylsilyloxymethyl)bi(dihydropyran)s as new protecting and resolving agents for 1,2-diols, J CHEM S P1, (12), 1999, pp. 1639-1645
Citations number
15
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
ISSN journal
0300922X → ACNP
Issue
12
Year of publication
1999
Pages
1639 - 1645
Database
ISI
SICI code
0300-922X(19990621):12<1639:DISP2P>2.0.ZU;2-P
Abstract
C-2 symmetric chiral 2,2'-bis(triisopropylsilyloxymethyl)bi(dihydropyran)s (S,S)-1 and (R,R)-1 were prepared from the corresponding glycidols and sele ctively reacted with 1,2-diols to give dispiroketals. The products of these reactions could be deprotected following treatment with fluoride, oxidatio n and reductive cleavage with samarium(II) iodide.