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

Article abstract of DOI:10.1016/S0040-4020(01)80529-9

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.