Reactions in the solid state. 4. Enantioselective photochemical reactions in crystalline inclusion compounds

The Photochemical Behavior of Colchicone and Thiocolchicone

“…The above-described reactivity shows some interesting features: (1) the conversion 5 → 7 represents, as the photochemical conversion of colchicine into ␣-, ␤-, and ␥-lumicolchicine, a new class of ␣-tropolone transposition: in fact, it is known that compound 10 can be converted into 11 (Scheme 4) ( [33][34][35] and that for this conversion a polar mechanism has been supposed; however, the photochemical conversion of colchicone cannot be explained on the basis of the same mechanism; (2) it is not clear the reason of the lack of reactivity of thiocolchicone.…”

meso- and rac-2,7-diphenyl-3,5-octadiyne-2,7-diol, C20H18O2

“…Structures of diyne-diols related to (I) have been reported by Toda and co-workers and have mainly involved clathrates of the three tetraaryl derivatives: 1,1,6,6-tetraphenylhexa-2,4-diyne-1,6-diol (Toda, Ward & Hart, 1981;Kaftory, Tanaka & Toda, 1985;Kaftory, 1987;Fukawa et al, 1989;Kaftory, Yagi, Tanaka & Toda, 1988;Toda, Tanaka, Kai et al, 1988;Toda, Tanaka, Asao et al, 1988), 1,1,6,6-tetrakis(3,4-dimethylphenyl)hexa-2,4-diyne-1,6-diol (Toda, Tanaka & Mak, 1985) and chiral 1,6-bis(2-chlorophenyl)-1,6-diphenylhexa-2,4-diyne-1,6-diol (Kaftory, 1987;Fujiwara, Tanaka, Tanaka & Toda, 1989;Toda, Tanaka & Mak, 1989;Fujiwara, Nanba, Hamada, Toda & Tanaka, 1990). …”

Structural Aspects and Templation of Photochemistry in Solid‐State Supramolecular Systems

“…This interpretation is supported by the crystal structure of the inclusion compound. 27 Another striking example is the stereo -and enantioselective photoreactions of the N , N -dialkylphenylglyoxylamides obtained as a result of irradiation solid inclusion compound of 43 in different optically active host compounds such as 3 , 5 , 9 , and 10 27,53 (Scheme 7.7 ). When a crystal of 43a and ( − ) -3 was irradiated, optically pure β -lactam( − ) -44a was obtained in 90% yield.…”