Preparation and Characterization of New C2‐ and C1‐Symmetric Nitrogen,Oxygen, Phosphorous,and Sulfur Derivatives and Analogs of TADDOL. Part II |
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Authors: | W. Bernd Schweizer Albert K. Beck Dieter Seebach |
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Affiliation: | 1. Laboratorium für Organische Chemie, Departement für Chemie und Angewandte Biowissenschaften, ETH‐Zürich, H?nggerberg HCI, Wolfgang‐Pauli‐Strasse 10, CH‐8093 Zürich, (phone: +41‐44‐632‐2990;2. fax: +41‐44‐632‐1144) |
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Abstract: | TADDOL (=α,α,α′,α′‐Tetraaryl‐1,3‐dioxolane‐4,5‐dimethanol) and the corresponding dichloride are converted to TADDAMINs (=(4S,5S)‐2,2,N,N′‐tetramethyl‐α,α,α′,α′‐tetraphenyl‐1,3‐dioxolan‐4,5‐dimethanamines) (Scheme 2) and ureas, 12 – 15 , and to TADDOP derivatives with seven‐membered O? P? O ester rings (Schemes 3 and 4). Cl/P‐Replacement via the Michaelis? Arbuzov reaction (Scheme 7) on mono‐ and dichlorides, derived from TADDOL, are described. It was not possible to obtain phosphines with the P‐atom attached to the benzhydrylic C‐atom of the TADDOL skeleton (Schemes 6 and 7). The X‐ray crystal structures (Figs. 1 and 2) of ten of the more than 30 new TADDOL derivatives are discussed. Full experimental details are presented. |
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Keywords: | TADDOL TADDAMIN TADDOP Sulfates Phosphonates Phosphoramidates Phosphites |
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