New silicon groups as potential chiral auxiliaries. Synthesis and highly selective chiral 1,6-induction in 1,2-additions to acylsilanes

Citation
S. Gassmann et al., New silicon groups as potential chiral auxiliaries. Synthesis and highly selective chiral 1,6-induction in 1,2-additions to acylsilanes, ORGANOMETAL, 20(9), 2001, pp. 1849-1859
Citations number
45
Language
INGLESE
art.tipo
Article
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANOMETALLICS
ISSN journal
0276-7333 → ACNP
Volume
20
Issue
9
Year of publication
2001
Pages
1849 - 1859
Database
ISI
SICI code
0276-7333(20010430)20:9<1849:NSGAPC>2.0.ZU;2-7
Abstract
Chiral silicon groups possessing an asymmetric and chelating alkoxymethyl s ubstituent at silicon have been prepared, and it was shown that these group s may have substantial utility as stereodirecting auxiliaries. For the 1,2- addition of organometallic species to chiral acylsilanes, auxiliaries with a single stereogenic center at position 6 with respect to the reactive carb onyl C atom proved particularly valuable. Compounds with such auxiliaries a re easily accessible in enantiomerically pure form, and the chiral groups i nduce pi -facial selectivities of as high as 98:2. In an example it is show n that chiral 1,6-induction may dominate over 1,5-induction.