207503-57-9Relevant articles and documents
Catalytic Asymmetric Crotylation of Aldehydes: Application in Total Synthesis of (-)-Elisabethadione
O'Hora, Paul S.,Incerti-Pradillos, Celia A.,Kabeshov, Mikhail A.,Shipilovskikh, Sergei A.,Rubtsov, Aleksandr E.,Elsegood, Mark R. J.,Malkov, Andrei V.
supporting information, p. 4551 - 4555 (2015/03/18)
A new, highly efficient Lewis base catalyst for a practical enantio- and diastereoselective crotylation of unsaturated aldehydes with E- and Z-crotyltrichlorosilanes has been developed. The method was employed as a key step in a novel asymmetric synthesis of bioactive serrulatane diterpene (-)-elisabethadione. Other strategic reactions for setting up the stereogenic centers included anionic oxy-Cope rearrangement and cationic cyclization. The synthetic route relies on simple, high yielding reactions and avoids use of protecting groups or chiral auxiliaries.
A more comprehensive and highly practical solution to enantioselective aldehyde crotylation
Kim, Hyunwoo,Ho, Stephen,Leighton, James L.
supporting information; experimental part, p. 6517 - 6520 (2011/06/22)
The enantioselective crotylation of aldehydes with 1,2- diaminochlorocrotylsilane reagents is effectively catalyzed by Sc(OTf) 3. The one significant limitation on the utility of these reagents-substrate scope-has thus been addressed. The net r
Chiral sulfoxides as activators of allyl trichlorosilanes in the stereoselective allylation of aldehydes
De Sio, Vincenzo,Massa, Antonio,Scettri, Arrigo
scheme or table, p. 3055 - 3059 (2010/09/06)
Chiral aryl methyl sulfoxides proved to be efficient activators in the asymmetric allylation of aldehydes with allyl trichlorosilanes. High enantioselectivity was found in the case of electron-poor aldehydes. The high levels of diastereoselectivity and th
