[1,2]-Wittig Rearrangement of Acetals III [1]. New 1,2-Alkoxyalcohols, 1,2-Alkoxyaminesand 1,2-Dialkoxy Compounds as Chiral Ligands for Organomagnesium and Organolithium Compounds and forLithium Aluminum Hydride |
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Authors: | Peter Gärtner Martin Letschnig Max Knollmüller |
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Institution: | Institut für Organische Chemie, Technische Universit?t Wien, A-1060 Wien, Austria, AT
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Abstract: | Summary. Eight O-substituted 1,2-diols and one O,N-substituted 1,2-aminoalcohol derived from 2-alkoxyoctahydro-7,8,8-trimethyl-4,7-methanobenzofurans
via a 1,2]-Witting rearrangement and subsequent substitution were synthesized and tested as additives for the enantioselective addition of butyllithium
and butylmagnesium chloride to benzaldehyde and for the reduction of acetophenone with lithium aluminum hydride. The selectivity
of the reactions was determined by GC of the obtained 1-phenyl-1-pentanol and 1-phenylethanol on a chiral phase. Best results
with regard to selectivity (52% ee and 94% ee, resp.) were achieved in the formation of 1-phenyl-1-pentanol by addition of the substituted 1,2-aminoalcohol to the organometallic
reagent and in the reduction of acetophenone using an α-alkoxyalcohol (62%ee).
Received March 10, 2000. Accepted March 23, 2000 |
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Keywords: | , ,Acetals, [1,2]-Wittig rearrangement, Ligands,chiral, Carbonyl addition,stereoselective, |
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