Enantiomeric differentiation by chiral macrocyclic polyethers derived from D-mannitol and binaphthol

Enantiomeric Recognition of Amine Compounds by Chiral Macrocyclic Receptors

“…26,27 Among them, DD-( 120) and (R)-and (S)-D-(121) (Chart 16) showed the highest degree of enantiomeric differentiation examined based on 1 H NMR spectroscopic data in CDCl 3 . 26,27,[152][153][154][155] Later, other macrocycles having carbohydrates attached were synthesized and studied by Pietraszkiewicz, Joly, and their co-workers. 40,[156][157][158] The chiral recognition data involving these macrocycles are summarized in Table 10.…”

“…An examination of CPK molecular models has shown that two bindable functional groups of the ammonium guests can be located in two binding sites of 148 in a complementary manner. 164 Of three macrocycles each containing a 9,9′-spirobifluorene group (151)(152)(153), the five-oxygen-containing 152 had the highest degree of enantioselectivity. 163,167,168…”

“…Natural compounds, such as carbohydrates, provide relatively inexpensive chiral starting materials for synthesis of optically active macrocycles. Syntheses and properties of chiral macrocyclic compounds having carbohydrates incorporated were summarized by Stoddart. , Among them, dd -( 120 ) and ( R )- and ( S )- d -( 121 ) (Chart ) showed the highest degree of enantiomeric differentiation examined based on 1 H NMR spectroscopic data in CDCl 3 . ,,− Later, other macrocycles having carbohydrates attached were synthesized and studied by Pietraszkiewicz, Joly, and their co-workers. ,− The chiral recognition data involving these macrocycles are summarized in Table .

16 Macrocycles 120 − 138

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1,1‘-Binaphthyl Dimers, Oligomers, and Polymers: Molecular Recognition, Asymmetric Catalysis, and New Materials

“…The rhodium and ruthenium complexes of ( S )- 5 are used in catalytic asymmetric hydrogenations. − The Lewis acid complexes of ( R )- 6 are used in an asymmetric hetero-Diels−Alder reaction as well as an asymmetric Claisen rearrangement . The titanium(IV) complexes of ( R )- 7 are used in asymmetric aldol condensations. , Chiral metallocene complexes prepared from ( S )- 8 have also been studied. , The enantioselective complexation of the binaphthyl-based crown ethers ( S )- 9 , ( S )- 10 , , and ( S )- 11 with various chiral guest molecules has been investigated.

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“…23,24 Chiral metallocene complexes prepared from (S)-8 have also been studied. 25,26 The enantioselective complexation of the binaphthyl-based crown ethers (S)-9, 27 (S)-10, 28,29 and (S)-11 30 with various chiral guest molecules has been investigated.…”