- Stereoselective synthesis of anti-1,3-diols via allylboration
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Allylboration of β-hydroxy aldehydes and ketones with allylboronic acid at room temperature produces the corresponding anti-1,3-diols as the major products.
- Kabalka, George W.,Narayana,Reddy, N. Kesavulu
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p. 2181 - 2184
(2007/10/03)
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- β-Substituted Organolithium Compounds from Chlorohydrins: Application to the Direct Synthesis of Bifunctionalized Organic Cpmpounds
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The reaction of different chlorohydrins with n-butyl-lithium at -78 deg C followed by metallation wiht lithium naphthalenide at the same temperature leads to very reactive organolithium compounds bearing an alkoxide function at the β-position with respect to metal.The reaction of these intermediates with several electriphiles leads to mono- as well as bi-functionalized organic compounds.Thus, treatment of these dianions with deuterium oxide, oxygen, carbon dioxide, benzyl bromide, dimethyl disulphide, and carbonyl compounds, gave 2-deuterioalcohols, 1,2-diols, β-hydroxy-acids, 2-benzyl alcohols, 2-hydroxy-thioethers, and 1,3-diols respectively.The preparation of β-substituted organolithium derivatives can be alternatively carried out starting from α-chloroketones by the same procedure.When the lithium atom is linked to a secondary carbon atom the dianions are very unstable and decompose, even at -100 deg C, by β-elimination yielding the corresponding olefins.
- Barluenga, Jose,Florez, Josefa,Yus, Miguel
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p. 3019 - 3026
(2007/10/02)
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