A highly diastereoselective Tandem radical reaction. Facile three-component routes to protected (E)-polysubstituted homoallylic alcohols |
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Authors: | Yeong-Jiunn Jang |
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Institution: | Department of Chemistry, National Taiwan Normal University 88, Sec. 4, Tingchow Road, Taipei 116, Taiwan, ROC |
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Abstract: | A facile synthesis of geometrically pure (E)-1,2,4-trisubstituted and (E)-1,2,4-tetrasubstituted homoallylic benzoates was developed. Various Lewis acids were subsequently evaluated in the diastereoselective radical substitution of (E)-β-nitrostyrene, and Titanium (IV) 2-ethylhexoxide emerged as the best Lewis acid in terms of yield and diastereoselectivity (up to 98% de). These reactions occurred with high regio-, diastereo- and stereoselectivity, and a possible mechanism to explain this transformation was proposed. |
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Keywords: | Radical Diastereoselective (E)-β-Nitrostyrene Homoallylic alcohol |
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