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


Gassmann, Sandra; Guintchin, Boris; Bienz, Stefan (2001). New silicon groups as potential chiral auxiliaries. Synthesis and highly selective chiral 1,6-induction in 1,2-additions to acylsilanes. Organometallics, 20(9):1849-1859.

Abstract

Chiral silicon groups possessing an asymmetric and chelating alkoxymethyl substituent at silicon have been prepared, and it was shown that these groups 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 carbonyl C atom proved particularly valuable. Compounds with such auxiliaries are easily accessible in enantiomerically pure form, and the chiral groups induce ð-facial selectivities of as high as 98:2. In an example it is shown that chiral 1,6-induction may dominate over 1,5-induction

Abstract

Chiral silicon groups possessing an asymmetric and chelating alkoxymethyl substituent at silicon have been prepared, and it was shown that these groups 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 carbonyl C atom proved particularly valuable. Compounds with such auxiliaries are easily accessible in enantiomerically pure form, and the chiral groups induce ð-facial selectivities of as high as 98:2. In an example it is shown that chiral 1,6-induction may dominate over 1,5-induction

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:2001
Deposited On:23 Aug 2017 16:35
Last Modified:23 Aug 2017 16:35
Publisher:American Chemical Society (ACS)
ISSN:0276-7333
Publisher DOI:https://doi.org/10.1021/om000970v

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