A divergent synthesis of cyclitol derivatives has been developed utilizing N-heterocyclic carbene-catalyzed benzoin-type cyclization of C 2-symmetric dialdoses. The resulting inososes are versatile intermediates, which are readily converted into not only inositols but also amino-, deoxy-, O-methyl-, and C-methyl-inositols.

The synthesis of cyclitol derivatives from C 2-symmetrical dialdoses is reported. The tetrabenzyl dialdose from D-mannitol or L-iditol furnishes the allo-inosose (II) or myo-inosose (III), resp. as a single diastereomer. -(KANG, B.; SUTOU, T.; WANG, Y.; KUWANO, S.; YAMAOKA, Y.; TAKASU*, K.; YAMADA, K.-I.; Adv. Synth. Catal. 357 (2015) 1, 131-147, http://dx.doi.org/10.1002/adsc.201400712 ; Grad. Sch. Pharm. Sci., Kyoto Univ., Sakyo, Kyoto 606, Japan; Eng.) -B. Bergmann 22-074