147700-67-2Relevant academic research and scientific papers
Derivatives of α,α,α′,α′-Tetraaryl-2,2-dimethyl-1,3- Dioxolan-4,5-Dimethanol (TADDOL) containing nitrogen, sulfur, and phosphorus atoms. New ligands and auxiliaries for enantioselective reactions
Seebach, Dieter,Hayakawa, Michiya,Sakaki, Jun-Ichi,Schweizer, W. Bernd
, p. 1711 - 1724 (1993)
α,α,α′,α′-Tetraaryl-2,2-dimethyl-l,3 - dioxolan-4,5-dimethanols are converted to bicyclic phosphites and phosphonites (2a-2e) by reaction with Cl2PR and Cl2POR derivatives. - One or both OH groups of the parent TADDOL can be replaced by Cl (→, 4a, 5a), and the halide in turn substituted by azide (→ 4b, 5b), thiocyanide (→ 6), or sulfide (→ 8). Reduction of the azido group(s) to NH2 and N-alkylation or acylation furnishes a variety of amino alcohols (4c-4f) and diamines (5c-5f), as well as a bis(trifluoroacetamide) (5g). Cyclization of the aminoalcohol (4c) produces a bicyclic system (7), containing a pyrrolidine ring (structure determination by X-ray diffraction). - The new chiral compounds containing nitrogen and phosphorus atoms might be useful ligands and auxiliaries for enantioselective syntheses.
Preparation of TADDOL derivatives for new applications
Seebach, Dieter,Pichota, Arkadius,Beck, Albert K.,Pinkerton, Anthony B.,Litz, Thomas,Karjalainen, Jaana,Gramlich, Volker
, p. 55 - 58 (1999)
(equation presented) TADDOL Substitution of one or both TADDOL OH groups by other functional groups X, Y is key to new applications of this cheap chiral auxiliary. The Appel reaction and treatment with SOCl2 provide the mono-and dichlorides, respectively. The chlorides are, in turn, replaced by various nucleophiles, and further modifications give a large variety of derivatives, including mono-and ditritylated dioxolanes. The new compounds -available in either enantiomeric form - are ready to be used in enantioselective synthesis and as dopants in liquid crystals.
Preparation and characterization of new C2- and C 1-symmetric nitrogen, oxygen, phosphorous, and sulfur derivatives and analogs of TADDOL. part i
Pichota, Arkadius,Gramlich, Volker,Beck, Albert K.,Seebach, Dieter
experimental part, p. 1239 - 1272 (2012/09/21)
The chloro alcohols 4-6 derived from TADDOLs (=α,α, α′,α′-tetraaryl-1,3-dioxolan-4,5-dimethanols) are used to prepare corresponding sulfanyl alcohols, ethers, and amines (Scheme 1 and Table 1). The dithiol analog of TADDOL and derivatives thereof, 45-49,
TADDOLs on their way to late transition metal complexes - synthesis and crystal structure of N- and S-containing TADDOL-derived compounds
Seebach, Dieter,Beck, Albert K.,Hayakawa, Michiya,Jaeschke, Georg,Kuehnle, Florian N. M.,et al.
, p. 315 - 332 (2007/10/03)
As a part of our research program aimed at the synthesis of TADDOL-derived ligands with heteroatoms other than oxygen as chelating units, we describe here new or improved routes to amino TADDOL-analogs (4, 5, 17-19, 21, 22, 26, 34 and 35) and thio-TADDOL-analogs (27-30 and 32).The sulfinato-thiolato Pt-complex 44 was prepared by an oxidative insertion of Pt into the S-S-bond of the corresponding thiosulfinate 29.Furthermore, the X-ray crystal structures of some of the new compounds (2-5, 28, 29, 32, 42 and 44) are presented and discussed. - Keywords: TADDOL derivative; chiral ligand; X-ray structure; platinum complex
