Chemists endeavor to develop efficient methods for the generation of carbon-carbon double bonds in organic and biomolecules with stereospecificity. [1] The outcomes benefit synthetic and natural product chemistry to a great extent. Herein, we contribute a new method to form the C=C bond that is complementary to existing methods. Some of the prominent methods include the coupling of aldehydes with organic phosphonium halides in the Wittig reaction, [2] the coupling of two aldehydes in the McMurry reaction, [3] the decomposition of cyclic thionocarbonates in the Corey-Winter reaction, [4,5] the decomposition of cyclic 2-alkoxy-1,3-dioxolanes in the Eastwood olefination, [5] the deoxygenation of epoxides, [1] and so forth. Alternatively, the C=C bond can be generated by 1,2-elimination reactions of substrates containing various functional groups. These substrates could be b-silyl alcohols in the Peterson olefination, [6] bisdithiocarbonates in the Barton deoxygenation, [5] 1,2-dihalides with zinc in DMSO, [1] or 1,2-diols and their derivatives under reductive conditions. [1] However, disadvantages and limitations exist in some of these methods, [1,3,5] such as demands on toxic reagents, incompatibility of other reducible functional groups with the applied strong reducing reagents, the lack of stereospecific control when forming the C=C bond, and so forth.
Herein, we report our success in the development of a novel benzyne-induced method for the generation of a C=C bond from b-amino alcohols. To the best of our knowledge, this method has never been reported. The use of b-amino alcohol as the starting material offers great advantages: some are commercially available, many come from natural sources, [7,8] and a number of them can be derived from natural a-amino acids. [9] In addition, we report our application of this new method as the key step in an efficient total synthesis of (À)-1-deoxy-d-fructose, which possesses biological and optical activities.