Thermal & photochemical reactions in the solid state by Fumio Toda

By Fumio Toda

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Very interestingly, irradiation of 160 in the inclusion complexes with 10b and 10c gave (–)-161 and (+)-162, respectively, in almost enantiomerically pure forms. In the complex with 10b and 10c, ethyl and methyl groups reacted to give (–)-161 and (+)-162, respectively. The reason for the difference was studied by X-ray analysis [37]. Irradiation of a 2:1 complex of 10c and 163a for 8 h gave (–)-164a of 97% ee in 52% yield [38]. Similar irradiation of a 1:1 complex of 10b and 163b for 20 h Table 15 Enantioselective photocyclization of anilides and glyoylamide in their 1:1 inclusion complexes with 10b or 10c Host 10b 10c 10b 10c 10b 10c 10b 10c Guest 154 154 156 156 158 158 160 160 Irradiation time (h) 150 150 50 50 15 15 53 58 Product (–)-155 (+)-155 (+)-157 (–)-157 (–)-159 (+)-159 (–)-161 (+)-162 Yield (%) Optical purity (% ee) 46 29 62 70 64 41 21 48 98 95 70 98 98 8 99 98 36 F.

In the case of the inclusion complexation between 10c and 149e, the two inclusion compounds 10c–149e (1:1) and 10c–149e (2:1) were formed by mixing of powdered 10c and 149e in 1:1 and 2:1 ratios, respectively. Irradiation of the 1:1 and 2:1 complexes gave the same product (–)-150e in 49% and 54% ee, respectively. However, recrystallization of 10c and 149e from toluene gave only the 2:1 complex, and its photoreaction gave (+)-150e of 98% ee in 77% yield (Table 13) [33]. Enantiocontrol of the photocyclization of N-methyl-N-phenyl-3-amino-2cyclohexen-1-one (151a,b) to the corresponding N-methylhexahydro-4-carbazolones (153a,b) via the dipolar ionic intermediate (152a,b) (Scheme 22) was also accomplished by photoirradiation of 1:1 inclusion complexes of 151a,b with the chiral hosts 10a–c.

This reaction was found to proceed in a single crystal-to-single crystal manner. The mechanism of the reaction was studied by X-ray crystal structural analysis [41]. Thermal and Photochemical Reactions in the Solid State 37 Scheme 24 Single crystal-to-single crystal enantioselective photodimerizations of coumarin (169a) and thiocoumarin (169b) were found to proceed efficiently in inclusion complexes with 10a and 10b, respectively [42]. By these reactions, (–)-anti-head-to-head dimers 170a and (+)-anti-head-to-head dimer 170b were obtained in optically pure forms.

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