Journal
ORGANIC LETTERS
Volume 2, Issue 16, Pages 2443-2445Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol006099w
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[GRAPHICS] In HMPA-THF solution, lithiated 1-naphthylacetonitrile undergoes highly syn-selective addition to aromatic aldehydes, providing the first access to such syn-aldols. Syn-selectivity is also observed with two other arylacetonitriles, Aldolate equilibration and crossover experiments demonstrate that HMPA promotes retro aldol reaction and that aldol diastereoselectivity under these conditions is thermodynamically controlled.
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