A practical improvement of crystallization-induced asymmetric transformation of allene-1,3-dicarboxylates

State of the Art in Crystallization‐Induced Diastereomer Transformations

“…However, the described CIDT procedure towards ( R )‐ 151 a required three repetitive crystallizations at −20 °C and was difficult to reproduce. Therefore in 2006 the same group elaborated an improved protocol based on analogous (−)‐bornyl and (−)‐isobornyl esters 151 b , c , respectively [124] . These provided more rigid crystal structures and CIDT could be successfully performed in hexane at room temperature.…”

The first highly stereoselective approach to the mitotic kinesin Eg5 inhibitor HR22C16 and its analogues

“…e l s e v i e r . c o m / l o c a t e / t e t a s y process via crystal-induced asymmetric transformation (CIAT) [26][27][28][29][30][31][32][33][34][35][36][37][38] in a mixed solvent of toluene and nitromethane afforded cis-4a-HCl in 93% yield and with 98% de. However, high trans-stereoselectivity rather than cis-stereoselectivity is required to satisfy the absolute configurations of the two stereogenic centers of the title compounds HR22C16 and its analogues.…”

Isocyanide-Induced Annulation Leading to Cyclopento-, Methano-, and Cyclopentano-[60]Fullerene Derivatives

“…Replacing the triple bond with cumulated double bonds, we performed the reaction of C 60 , t BuNC, and the allenoate counterpart of DMAD. Dimethyl 2,3-pentadienedioate 12a reacted with C 60 and t BuNC and yielded only one isolable product, later identified as the 13a (Figures S74–S79), with water involved in this process. Ethyl buta-2,3-dienoate 12b underwent a similar four-component annulation to form 13b (Figures S80–S85).…”