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Resolution and absolute configuration of 1, 3-dimethylallene

✍ Scribed by William L. Waters; Marjorie C. Caserio

Publisher: Elsevier Science
Year: 1968
Tongue: French
Weight: 187 KB
Volume: 9
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)89830-5

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✦ Synopsis

We wish to report a simple one-step method for the partial resolution of racemic allenes based on the procedure of asymmetric hydroboration developed by H. C. Brown and coworkers(').

Hydroboration of (-)-a-pinene in diglyme leads to (+)-sym-tetraisopinocampheyldiborane (lb) , I, which has been shown to be a highly stereoselective hydroborating agent and can be used to prepare certain optically active alcohols and alkenes in high optical purity(lc).

Utilizing this reagent for the hydroboration of excess 1,3-dimethylallene, II, we anticipated that the recoverable allene would be enriched in one enantiomer. This was confirmed by experiment Ina typical run, a suspension of (+)-I in . .BH 1 CH,

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