Chelation vs. non-chelation control in addition reactions of ethylmetallic reagents to acrolein dimer
- 1 February 1988
- journal article
- research article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 66 (2) , 209-213
- https://doi.org/10.1139/v88-035
Abstract
Reactions of 3,4-dihydro-2H-pyran-2-carboxaldehyde (acrolein dimer) with ethylmetallics based on lithium, titanium, and copper were examined for stereoselectivity. High selectivity (92:8) was found for non-chelation controlled addition yielding the erythro product when ethyllithium was employed in the presence of BF3•OEt2. High selectivity (89:11) for products of chelation controlled addition (threo) was observed for ethylcopper reagents in the presence of magnesium salts. Titanium reagents yielded mixtures rich in products of either chelation or non-chelation controlled addition depending on the titanium substituents. In no cases were stereoselectivities obtained with titanium reagents better than those obtained by use of the aforementioned lithium and copper reagents.This publication has 13 references indexed in Scilit:
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