Author:
Singh Shankar M.,Oehlschlager Allan C.
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.
Publisher
Canadian Science Publishing
Subject
Organic Chemistry,General Chemistry,Catalysis
Cited by
20 articles.
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