727381-82-0Relevant academic research and scientific papers
Design of new chiral phase-transfer catalysts with dual functions for highly enantioselective epoxidation of α,β-unsaturated ketones
Ooi, Takashi,Ohara, Daisuke,Tamura, Masazumi,Maruoka, Keiji
, p. 6844 - 6845 (2004)
A new chiral ammonium bromide, 1-Br, possessing diarylmethanol functionality as a substrate recognition site has been designed as a promising, dual-functioning catalyst for the highly enantioselective epoxidation of α,β-unsaturated ketones under mild phas
Catalytic enantioselective addition of alkylzirconium reagents to aliphatic aldehydes
Carter, Nicholas,González-Soria, María José,Maciá, Beatriz,Vaccari, Jade
, (2021/08/10)
A catalytic methodology for the enantioselective addition of alkylzirconium reagents to aliphatic aldehydes is reported here. The versatile and readily accessible chiral Ph-BINMOL ligand, in the presence of Ti(OiPr)4 and a zinc salt, facilitates the reaction, which proceeds under mild conditions and is compatible with functionalized nucleophiles. The alkylzirconium reagents are conveniently generated in situ by hydrozirconation of alkenes with the Schwartz reagent. This work is a continuation of our previous work on aromatic aldehydes.
Enantioselective alkylation of aldehydes using functionalized alkylboron reagents catalyzed by a chiral titanium complex
Kumar, Ravindra,Kawasaki, Hiroki,Harada, Toshiro
supporting information, p. 4198 - 4201 (2013/09/12)
A practical method is developed for the synthesis of enantioenriched functionalized secondary alcohols through catalytic enantioselective alkylation of aldehydes. Functionalized alkylboron reagents, [FG-(CH2) n]3B (FG = Br, TIPSO, PhtN, CO2iPr, and CN) prepared from terminal olefin precursors by hydroboration, undergo enantioselective addition to aldehydes in the presence of a catalytic amount (5 mol %) of 3-(3,5-diphenylphenyl)-H8-BINOL and excess titanium tetraisopropoxide to afford the corresponding functionalized alcohols in high enantioselectivities up to 99% ee.
Lithiated carbamates: Chiral carbenoids for iterative homologation of boranes and boronic esters
Stymiest, Jake L.,Dutheuil, Guillaume,Mahmood, Adeem,Aggarwal, Varinder K.
, p. 7491 - 7494 (2008/09/17)
(Chemical Equation Presented) Take your pick: Either enantiomer of either diastereomer of substrates bearing adjacent stereogenic centers is accessible through reaction of an (R)- or (S)-lithiated carbamate with an (R)- or (S)-boronic ester (see scheme; pin = pinacolate, OCb = substituted carbamate).
Baker's yeast reduction of arylalkyl and arylalkenil γ- and δ-keto acids
Aquino, Mario,Cardani, Silvia,Fronza, Giovanni,Fuganti, Claudio,Fernandez, Rosalino Pulido,Tagliani, Auro
, p. 7887 - 7896 (2007/10/02)
γ- and δ-Lactones 5, 6, 13, 14, 15 and 16 were synthesized via baker's yeast reduction of the corresponding keto acids 3, 4 and 9-12. The enantioselectivity of the reduction is strongly dependent on the nature of the keto acid; the δ-lactones ware always obtained in an ee% higher than the γ-lactones and ranging from 70% to 100%.
