213843-95-9Relevant academic research and scientific papers
Ni-Catalyzed Asymmetric Cycloisomerization of Dienes by Using TADDOL Phosphoramidites
Schmitz, Christian,Leitner, Walter,Franciò, Giancarlo
supporting information, p. 10696 - 10702 (2015/07/20)
A library of α,α,α,α-tetraaryl-1,3-dioxolane-4,5-dimethanol (TADDOL)-based phosphoramidites has been synthesized and applied in the Ni-catalyzed cycloisomerization of different dienes. Through the systematic variation of the three structural motifs of the
Preparation and characterization of new C2- and C 1-symmetric nitrogen, oxygen, phosphorous, and sulfur derivatives and analogs of TADDOL. part II
Pichota, Arkadius,Gramlich, Volker,Bichsel, Hans-Ulrich,Styner, Thomas,Knoepfel, Thomas,Wuensch, Ralf,Hintermann, Tobias,Schweizer, W. Bernd,Beck, Albert K.,Seebach, Dieter
experimental part, p. 1273 - 1302 (2012/10/07)
TADDOL (=α,α,α′,α′-Tetraaryl-1,3- dioxolane-4,5-dimethanol) and the corresponding dichloride are converted to TADDAMINs (=(4S,5S)-2,2,N,N′-tetramethyl-α,α,α′, α′-tetraphenyl-1,3-dioxolan-4,5-dimethanamines) (Scheme 2) and ureas, 12-15, and to TADDOP derivatives with seven-membered O-P-O ester rings (Schemes 3 and 4). Cl/P-Replacement via the Michaelis-Arbuzov reaction (Scheme 7) on mono- and dichlorides, derived from TADDOL, are described. It was not possible to obtain phosphines with the P-atom attached to the benzhydrylic C-atom of the TADDOL skeleton (Schemes 6 and 7). The X-ray crystal structures (Figs. 1 and 2) of ten of the more than 30 new TADDOL derivatives are discussed. Full experimental details are presented. Copyright
Development, mechanism, and scope of the palladium-catalyzed enantioselective allene diboration
Burks, Heather E.,Liu, Shubin,Morken, James P.
, p. 8766 - 8773 (2008/02/12)
In the presence of a chiral phosphoramidite ligand, the palladium-catalyzed diboration of allenes can be executed with high enantioselectivity. This reaction provides high levels of selectivity with a range of aromatic and aliphatic allene substrates. Iso
Enantioselective rhodium-catalyzed [2+2+2] cycloaddition of alkenyl isocyanates and terminal alkynes: Application to the total synthesis of (+)-lasubine II
Yu, Robert T.,Rovis, Tomislav
, p. 12370 - 12371 (2007/10/03)
The use of TADDOL-based phosphoramidite ligands on rhodium allows for the incorporation of terminal alkynes in the [2+2+2] cycloaddition with alkenyl isocyanates. Terminal aliphatic alkynes provide bicyclic lactams, while the use of aryl alkynes provides complementary access to vinylogous amides. Product selectivity seems to be governed by a combination of electronics and sterics, with smaller and/or more electron-deficient substituents favoring lactam formation. The use of homologous alkenyl isocyanates leads to an expedient asymmetric total synthesis of the alkaloid lasubine II. Copyright
