Journal
ORGANIC LETTERS
Volume 7, Issue 5, Pages 799-802Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol0476164
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- NIGMS NIH HHS [S06 GM 8102] Funding Source: Medline
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The asymmetric allenylboration of representative aldehydes with the stable, storable 1 is reported. Easily and efficiently prepared in either enantiomeric form from the air-stable crystalline 4 through simple Grignard procedures, 1 gives 6 cleanly. The latter is easily isolated in high yield and ee with predictable stereochemistry. The procedure also regenerates 4 for its direct conversion back to 1 and facilitates the efficient recovery of the pseudoephedrine. The net process is the synthetic equivalent of the asymmetric addition of allenylmagnesium bromide to aldehydes.
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