α,α,α′,α′‐Tetraaryl‐1,3‐dioxolane‐4,5‐dimethanols (TADDOLs) for Resolutions of Alcohols and as Chiral Solvating Agents in NMR Spectroscopy | Zendy

Von Dem BusscheHünnefeld Christoph | Zendy; Beck Albert K. | Zendy; Lengweiler Urs | Zendy; Seebach Dieter | Zendy

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α,α,α′,α′‐Tetraaryl‐1,3‐dioxolane‐4,5‐dimethanols (TADDOLs) for Resolutions of Alcohols and as Chiral Solvating Agents in NMR Spectroscopy

Author(s) -

Von Dem BusscheHünnefeld Christoph,

Beck Albert K.,

Lengweiler Urs,

Seebach Dieter

Publication year - 1992

Publication title -

helvetica chimica acta

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.74

H-Index - 82

eISSN - 1522-2675

pISSN - 0018-019X

DOI - 10.1002/hlca.19920750203

Subject(s) - chemistry , dioxolane , reagent , enantiomer , solvent , butyllithium , crystallization , derivative (finance) , nuclear magnetic resonance spectroscopy , organic chemistry , medicinal chemistry , economics , financial economics

The use of α,α,α′,α′ ‐tetraaryl‐1,3‐dioxolane‐4,5‐dimethanols ( = TADDOLs;1) as chiral NMR shift reagents ( 1 H, 13 C, 19 F) is described. In many cases, the ratio of enantiomeric alcohols and amines can be determined under standard conditions of measurement (CDCl 3 as solvent, room temperature). The preparation and use of a new type of TADDOL, the tetrakis(dimethylamino) derivative 1d , is described. Menthol, octan‐2‐ol, and oct‐1‐yn‐3‐ol are partially resolved by crystallization of clathrates with 1c and 1d .

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