27345-72-8Relevant articles and documents
Applying the Bent Bond/Antiperiplanar Hypothesis to the Stereoselective Glycosylation of Bicyclic Furanosides
Parent, Jean-Fran?ois,Bertrand, Xavier,Deslongchamps, Ghislain,Deslongchamps, Pierre
, p. 758 - 773 (2020/01/11)
The glycosylation stereoselectivities for a series of bicyclic furanoside models have been carried out in the presence of weak nucleophiles. These results were analyzed through the bent bond/antiperiplanar hypothesis (BBAH) orbital model to test its validity. According to the BBAH, incoming nucleophiles displace one of the two bent bonds of bicyclic oxocarbenium ion intermediates in an antiperiplanar fashion. The glycosylation stereoselectivity is then governed by the displacement of the weaker bent bond as determined by the presence of electron-withdrawing or -donating substituents at C2. Overall, the BBAH analysis expands Woerpel's "inside/outside attack" glycosylation model by considering the stereoelectronic influence of neighboring electron-withdrawing and -donating groups on the nucleophilic addition to oxocarbenium ion intermediates.
Asymmetric reduction of substituted indanones and tetralones catalyzed by chiral dendrimer and its application to the synthesis of (+)-sertraline
Wang, Guangyin,Zheng, Changwu,Zhao, Gang
, p. 2074 - 2081 (2007/10/03)
A recoverable dendrimeric supported prolinol was used as a catalyst in the asymmetric reduction of indanones and tetralones to give separable cis and trans isomers up to 97% ee. This method was also applied in the enantioselective synthesis of the antidepressant drug (+)-sertraline.
PREPARATION OF 7-OXABICYCLONONANES AND 2-OXABICYCLODECANES SPECIFICALLY LABELLED WITH DEUTERIUM
Turecek, Frantisek
, p. 858 - 876 (2007/10/02)
trans-Annulated 7-oxabicyclononanes, labelled with deuterium at C(1), C(6), C(8) and C(9), and cis-annulated isomers labelled at C(1) and C(6) were prepared by cyclization of the cor
