Synthesis of diastereometrically pure cubane-like photodimers from 2,4-pentanediyl-bis-2-naphthoates??

Photochemical & Photobiological Sciences Pub Date: 2013-10-31 DOI: 10.1039/C3PP50326G

Abstract

Irradiation of (2R,4R)-(?)- and (2S,4S)-(+)-2,4-pentanediyl-bis-2-naphthoates (1R and 1S, respectively) in organic solutions exclusively results in cubane-like antiHH photodimers in 100% yield. Asymmetric induction with 100% diastereometric excess (de) has been achieved and the absolute configuration of the yielded diastereomers has been established. Moreover, irradiation of (2R,4S)-2,4-pentanediyl-bis-2-naphthoate (1M) gives cubane-like synHH photodimers in 100% yield.

Graphical abstract: Synthesis of diastereometrically pure cubane-like photodimers from 2,4-pentanediyl-bis-2-naphthoates
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