Chiral Transfer in the Reaction of Aminoallylic Stannanes with Carbonyls in Two Different Modes using Tin(II) and Indium(III) Halides for the Synthesis of Each Enantiomer

The reaction of homochiral aminoallylic stannanes with aldehydes gave carbonyl adducts of amino alcohols in the presence of either SnCl2 or InBr3. Both additives afforded the products in opposite absolute stereochemical configurations. The controlled chirality was ascribed to the different transmeta...

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Bibliographic Details
Published in:Organometallics 2014-08, Vol.33 (15), p.3924-3927
Main Authors: Yasuda, Makoto, Nagano, Yoshitaka, Yunoki, Hiroshi, Tsuruwa, Kensuke, Baba, Akio
Format: Article
Language:English
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Summary:The reaction of homochiral aminoallylic stannanes with aldehydes gave carbonyl adducts of amino alcohols in the presence of either SnCl2 or InBr3. Both additives afforded the products in opposite absolute stereochemical configurations. The controlled chirality was ascribed to the different transmetalation pathways of SnCl2 and InBr3.
ISSN:0276-7333
1520-6041
DOI:10.1021/om500768e