Stereoselectivity in nucleophilic additions to 3-azidoalkanals |
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| Authors: | Huh Chan Woo Schroeder Chad Singh Gurpreet Aubé Jeffrey |
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| Affiliation: | The University of Kansas Chemical Methodologies and Library Development Center, 2034 Becker Dr., Delbert M. Shankel Structural Biology Center, Lawrence, Kansas 66047, USA. |
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| Abstract: | The stereoselectivity of nucleophilic additions to 3-azidoalkanals was investigated. Non-chelating, BF(3)·OEt(2)-mediated Sakurai addition to 3-azidoalkanals afforded 1,3-anti products, whereas use of a chelating Lewis acid, TiCl(4), resulted in 1,3-syn products with moderate selectivity. A boat-like chelation structure of the 3-azidoalkanal with the Lewis acid is proposed to be consistent with the 1,3-syn selectivity of the reactions. Mukaiyama aldol addition to 3-azidohexanal generated 1,3-anti products regardless of the chelating ability of the Lewis acid. |
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