870273-44-2Relevant articles and documents
A new model of light-powered chiral molecular motor with higher speed of rotation, part 1 - Synthesis and absolute stereostructure
Fujita, Takuma,Kuwahara, Shunsuke,Harada, Nobuyuki
, p. 4533 - 4543 (2005)
To develop a molecular motor with a higher speed of rotation, a new model light-powered chiral molecular motor 2 of five-membered ring type was designed, and the motor rotation isomers (-)-2a and (-)-2c were directly synthesized in enantiopure forms for the first time from the ketone (+)-8. The precursor alcohols 9 and 10 were enantioresolved by the camphorsultam-dichlorophthalic acid (CSDP acid; 3) method, and their absolute configurations were determined by X-ray crystallographic analysis of the CSDP ester (-)-11b and chemical correlations. The enantiopure ketone (S)-(+)-8 formed from (1S,2S)-(+)-9 or (1R,2S)-(-)-10 was subjected to the McMurry reaction with TiCl 3/LiAlH4, yielding the motor rotation isomers [CD(-)257.8]-(2S,2′S)-(M,M)-(E)-(-)-2a and [CD(-)270.0]-(2S,2′S)-(M, M)-(Z)-(-)-2c. These studies enabled us unambiguously to determine the absolute stereo-structure of the motor 2, which is of critical importance for control over the direction of motor rotation. Wiley-VCH Verlag GmbH & Co. KGaA, 2005.