89358-10-1Relevant academic research and scientific papers
Tandem aldol-allylation and aldol-aldol reactions with ketone-derived enolsilanes: Highly diastereoselective single-step synthesis of complex tertiary carbinols
Wang, Xiaolun,Meng, Qinglin,Perl, Nicholas R.,Xu, Yue,Leighton, James L.
, p. 12806 - 12807 (2005)
A new tandem aldol-allylation reaction employing ketone-derived enolates has been developed that leads to the rapid, diastereoselective synthesis of tertiary carbinol containing fragments with relevance to polyketide natural product synthesis. In addition
Stereoselective synthesis of anti-1,3-diols via allylboration
Kabalka, George W.,Narayana,Reddy, N. Kesavulu
, p. 2181 - 2184 (1996)
Allylboration of β-hydroxy aldehydes and ketones with allylboronic acid at room temperature produces the corresponding anti-1,3-diols as the major products.
Indirect Tertiary Alcohol Enantiocontrol by Acylative Organocatalytic Kinetic Resolution
Amalian, Jean-Arthur,Bressy, Cyril,Charles, Laurence,Desrues, Titouan,Liu, Xueyang,Monnier, Valérie,Pons, Jean-Marc,Quintard, Adrien
supporting information, p. 4332 - 4336 (2021/06/27)
The stereocontrol of tertiary alcohols represents a recurrent challenge in organic synthesis. In the present paper, we describe a simple, efficient, and indirect method to enantioselectively prepare tertiary alcohols through a chiral isothiourea catalyzed
Sequenced Reactions with Samarium(II) Iodide. Domino Epoxide Ring-Opening/Ketyl Olefin Coupling Reactions
Molander, Gary A.,Losada, Carlos Del Pozo
, p. 2935 - 2943 (2007/10/03)
A new sequential reductive coupling process promoted by samarium(II) iodide is described. Cascade epoxide ring opening and ketyl radical olefin cyclization leads to a variety of cis-1,3-cyclopentanediols and cis-1,3-cyclohexanediols in good yields and with high diastereoselectivity.
β-Substituted Organolithium Compounds from Chlorohydrins: Application to the Direct Synthesis of Bifunctionalized Organic Cpmpounds
Barluenga, Jose,Florez, Josefa,Yus, Miguel
, p. 3019 - 3026 (2007/10/02)
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.
