Facile approach towards the synthesis of homochiral functionalised alcohols from 4-O-[(tert)-butyldimethylsilyl]-2,3-O-cyclohexylidene-l-threose of (l)-(+)-tartaric acid origin |
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| Institution: | 1. Key Laboratory of Thermal-Fluid Science and Engineering of MOE, School of Energy and Power Engineering, Xi''an Jiaotong University, 710049, China;2. Energy Research Institute at NTU (ERIAN), Nanyang Technological University, Singapore 639798, Singapore;3. School of Mechanical and Aerospace Engineering, Nanyang Technological University, Singapore 639798, Singapore |
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| Abstract: | (l)-(+)-Diethyl tartarate 2 has been transformed into the aldehyde 6. Grignard additions to 6 take place with moderate diastereoselectivity giving predominant formation of the anti products 8a–e. However, in each case the diastereoalcohols are easily separable by column chromatography giving rise to the formation of a series of functionalised homochiral alcohols 7 and 8. On the other hand Zn mediated allylation and propargylation of 6 in the presence of water proceeded efficiently with almost absolute (>99%) stereoselective formation of versatile functionalised homoallylic 8d and homopropargylic 8e alcohols respectively. |
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