Canadian journal of chemistry

Chelation vs. non-chelation control in addition reactions of ethylmetallic reagents to acrolein dimer

SM Singh, AC Oehlschlager

文献索引：Singh, Shankar M.; Oehlschlager, Allan C. Canadian Journal of Chemistry, 1988 , vol. 66, p. 209 - 213

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被引用次数: 7

摘要

Reactions of 3, 4-dihydro-2 H-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 BF3OEt2. High selectivity (89: 11) for products of chelation controlled addition (threo) was observed for ethylcopper reagents in the ...