Stereoselective reduction of β hydroxyketones to 1,3-diols highly selective 1,3-asymmetric induction via boron chelates

阅读量:

94

作者:

K NarasakaFC Pai

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摘要:

Highly selective asymmetric induction can be achieved in the reduction of acyclic β-hydroxyketones via boron chelates. Treatment of β-hydroxyketones ( 1) with tributyl or tri-isobutylborane and successively with sodium borohydride afforded syn-1,3-diols ( 3) in highly stereo-selective manner, Syn -α-substituted-β -hydroxyketones ( 8) were also reduced to give syn, syn-1,3-diols ( 9) exclusively. The reaction was further applied to the convenient preparation of 3-deoxy-hexoses.

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DOI:

10.1016/0040-4020(84)80006-X

被引量:

1067

年份:

1984

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