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Enantioconvergent hydroboration of a racemic allene: enantioselective synthesis of (E)-?-stannyl-anti-homoallylic alcohols via aldehyde crotylboration.

ABSTRACT: The enantioconvergent hydroboration of racemic allenylstannane (±)-1 with ((d)Ipc)(2)BH converts both enantiomers of (±)-1 into the enantioenriched crotylborane (S)-E-3. Subsequent crotylboration of aldehydes with (S)-E-3 provides (E)-stannyl-homoallylic alcohols 5 in good yields and with excellent enantioselectivity.

SUBMITTER: Chen M 

PROVIDER: S-EPMC3086366 | biostudies-literature | 2011 Apr

REPOSITORIES: biostudies-literature

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Enantioconvergent hydroboration of a racemic allene: enantioselective synthesis of (E)-δ-stannyl-anti-homoallylic alcohols via aldehyde crotylboration.

Chen Ming M   Roush William R WR  

Journal of the American Chemical Society 20110330 15

The enantioconvergent hydroboration of racemic allenylstannane (±)-1 with ((d)Ipc)(2)BH converts both enantiomers of (±)-1 into the enantioenriched crotylborane (S)-E-3. Subsequent crotylboration of aldehydes with (S)-E-3 provides (E)-stannyl-homoallylic alcohols 5 in good yields and with excellent enantioselectivity. ...[more]

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