1313875-02-3Relevant academic research and scientific papers
One-point binding ligands for asymmetric gold catalysis: Phosphoramidites with a TADDOL-related but acyclic backbone
Teller, Henrik,Corbet, Matthieu,Mantilli, Luca,Gopakumar, Gopinadhanpillai,Goddard, Richard,Thiel, Walter,Fuerstner, Alois
, p. 15331 - 15342 (2012/11/07)
Readily available phosphoramidites incorporating TADDOL-related diols with an acyclic backbone turned out to be excellent ligands for asymmetric gold catalysis, allowing a number of mechanistically different transformations to be performed with good to outstanding enantioselectivities. This includes [2 + 2] and [4 + 2] cycloadditions of ene-allenes, cycloisomerizations of enynes, hydroarylation reactions with formation of indolines, as well as intramolecular hydroaminations and hydroalkoxylations of allenes. Their preparative relevance is underscored by an application to an efficient synthesis of the antidepressive drug candidate (-)-GSK 1360707. The distinctive design element of the new ligands is their acyclic dimethyl ether backbone in lieu of the (isopropylidene) acetal moiety characteristic for traditional TADDOLs. Crystallographic data in combination with computational studies allow the efficiency of the gold complexes endowed with such one-point binding ligands to be rationalized.
Concise synthesis of the antidepressive drug candidate GSK1360707 by a highly enantioselective gold-catalyzed enyne cycloisomerization reaction
Teller, Henrik,Fuerstner, Alois
, p. 7764 - 7767 (2011/08/06)
Out of depression: Indeed, no depressing results are obtained from a gold-catalyzed enyne cycloisomerization controlled by phosphoramidite ligands with TADDOL-related but acyclic backbones (see scheme; Cbz=benzyloxycarbonyl). The "triple-reuptake inhibito
Effects of nitrogen and alkene substitution on the PtCl2 catalyzed cycloisomerization of N-tethered 1,6-enyne precursors to the triple reuptake inhibitor GSK1360707
Elitzin, Vassil,Liu, Bing,Sharp, Matthew,Tabet, Elie
scheme or table, p. 3518 - 3520 (2011/07/09)
The effects of nitrogen and alkene substitution on the cycloisomerization of N-tethered 1,6-enynes into 3-azabicyclo[4.1.0]heptene precursors to the triple reuptake inhibitor GSK1360707 are described. In general, electron donating substituents proved bene
