208114-17-4Relevant academic research and scientific papers
Preparation of chiral sugar-derived fluorides using new nucleophilic fluorinating reagents
Bilska-Markowska, Monika,Koroniak, Henryk
, p. 185 - 192 (2017/09/18)
New fluorinating reagents, composed of (S)-2-(diphenylmethyl)pyrrolidine and 1,1,3,3,3-pentafluoropropene/hexafluoropropene, have been found to be an effective system for nucleophilic deoxyfluorination. Regio- and stereoselectivity of deoxyfluorination of sugar-derived allylic, benzylic and propargylic alcohols with new reagents have been studied.
Addition of alkynes to aldehydes and activated ketones catalyzed by rhodium-phosphine complexes
Dhondi, Pawan K.,Carberry, Patrick,Choi, Lydia B.,Chisholm, John D.
, p. 9590 - 9596 (2008/03/17)
(Chemical Equation Presented) A mixture of 2-(di-tert-butylphosphino) biphenyl and dicarbonylacetonato rhodium(I) provides an effective catalyst system for the addition of alkynes to aldehydes and activated ketones. In contrast to the more common zinc-cat
Applications of intramolecular cyclopropanations of chiral secondary allylic diazoacetates
Martin, Stephen F.,Hillier, Michael C.
, p. 41 - 55 (2007/10/03)
The diastereomeric secondary allylic diazoacetates 6a,b and 8a,b, which were readily prepared from the common intermediate 4, were cyclized in the presence of the achiral catalyst Cu(TBS)2 to furnish mixtures of the adducts 9a,b/10a,b and 12a,b/13a,b, respectively; in these cyclizations, the diastereoselectivity of the reaction was substrate controlled. When 6a,b and 8a,b were cyclized in the presence of the chiral catalysts Rh2[(5S)-MEPY]4 or Rh2[(5A)-MEPY]4, the substrate-based selectivity could be reversed if the chirality of the substrate and catalyst were matched. The advantages associated with the use of chiral catalysts to effect the diastereoselective cyclization of chiral allylic diazoacetates were demonstrated by the synthesis of 25, which comprises the cyclopropane subunit found in the diterpene ingol B (14).
Diastereodifferentiation in intramolecular cyclopropanations of chiral secondary allylic diazoacetates
Martin, Stephen F.,Hillier, Michael C.
, p. 2929 - 2932 (2007/10/03)
Intramolecular cyclopropanations of diastereomeric, secondary allylic diazoacetates were carried out in the presence of an achiral copper catalyst, Cu(TBS)2, and the chiral rhodium catalysts Rh2[5(S)-MEPY]4 and Rh2[5(R)- MEPY]4 to give diastereomeric cyclopropyl lactones in ratios that varied with catalyst and stereochemistry of the starting material.
