4.0 Article

Spiroborate esters in the borane-mediated asymmetric synthesis of pyridyl and related heterocyclic alcohols

Journal

TETRAHEDRON-ASYMMETRY
Volume 18, Issue 23, Pages 2738-2745

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetasy.2007.10.044

Keywords

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Funding

  1. NCRR NIH HHS [P20 RR016470] Funding Source: Medline
  2. NIGMS NIH HHS [S06 GM008216-250004, S06 GM008216] Funding Source: Medline

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The effectiveness of several spiroborate ester catalysts was investigated in the asymmetric borane reduction of 2-, 3-, and 4-acetylpyriclines under different reaction conditions. Highly enantiomerically enriched 1-(2-, 3-, and 4-pyridyl)ethanols and 1-(heterocyclic)ethanols were obtained using 1-10% catalytic loads of the spiroborate 5 derived from diphenylprolinol and ethylene glycol. (c) 2007 Elsevier Ltd. All rights reserved.

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