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1,n-Glycols as Dialdehyde Equivalents in Iridium-Catalyzed Enantioselective Carbonyl Allylation and Iterative Two-Directional Assembly of 1,3-Polyols

Authors

  • Yu Lu,

    1. University of Texas at Austin, Department of Chemistry and Biochemistry, 1 University Station—A5300, Austin, TX 78712-1167 (USA), Fax: (+1) 512-471-8696
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  • In Su Kim,

    1. University of Texas at Austin, Department of Chemistry and Biochemistry, 1 University Station—A5300, Austin, TX 78712-1167 (USA), Fax: (+1) 512-471-8696
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  • Abbas Hassan,

    1. University of Texas at Austin, Department of Chemistry and Biochemistry, 1 University Station—A5300, Austin, TX 78712-1167 (USA), Fax: (+1) 512-471-8696
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  • David J. Del Valle,

    1. University of Texas at Austin, Department of Chemistry and Biochemistry, 1 University Station—A5300, Austin, TX 78712-1167 (USA), Fax: (+1) 512-471-8696
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  • Michael J. Krische Prof.

    1. University of Texas at Austin, Department of Chemistry and Biochemistry, 1 University Station—A5300, Austin, TX 78712-1167 (USA), Fax: (+1) 512-471-8696
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  • Acknowledgement is made to Merck, the Robert A. Welch Foundation, the American Chemical Society Green Chemistry Institute Pharmaceutical Roundtable, the NIH (RO1-GM069445), the Korea Research Foundation (KRF-2007-356-E00037) (I.S.K.), and the Higher Education Commission of Pakistan (A.H.) for partial support of this research. Dr. Oliver Briel of Umicore is thanked for the generous donation of [{Ir(cod)Cl}2].

Abstract

Wirklich instabil? 1,n-Glycole wirken als Syntheseäquivalente für instabile Dialdehyde bei der bidirektionalen Carbonylallylierung ausgehend vom Alkohol-Oxidationsnivau unter iridiumkatalysierter Transferhydrierung. Eine iterative asymmetrische Allylierung mit 1,3-Propandiol ermöglicht den schnellen Aufbau geschützter 1,3-Polyolsubstrukturen mit außergewöhnlicher Stereokontrolle.

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