89358-10-1Relevant articles and documents
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
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
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.