104131-92-2Relevant academic research and scientific papers
Pd(II)-catalyzed enantioselective C-H activation of cyclopropanes
Wasa, Masayuki,Engle, Keary M.,Lin, David W.,Yoo, Eun Jeong,Yu, Jin-Quan
supporting information; experimental part, p. 19598 - 19601 (2012/01/17)
Systematic ligand development has led to the identification of novel mono-N-protected amino acid ligands for Pd(II)-catalyzed enantioselective C-H activation of cyclopropanes. A diverse range of organoboron reagents can be used as coupling partners, and the reaction proceeds under mild conditions. These results provide a new retrosynthetic disconnection for the construction of enantioenriched cis-substituted cyclopropanecarboxylic acids.
Deamination Reactions, 44. Decomposition of 1-Alkylcyclopropanediazonium Ions
Kirmse, Wolfgang,Rode, Jutta,Rode, Klaus
, p. 3672 - 3693 (2007/10/02)
1-Methyl- (17), 1,2-dimethyl- (41, 44), 1-propyl- (64), 1-(1-methylethyl)cyclopropanediazonium ions (80), and -1-diazonium ions (93) have been generated by alkaline cleavage of the analogous nitrosocarbamates in methanol.Cyclopropyl-allyl transformation and nucleophilic displacement were the only reactions of 17, 41, 44, and 93 while elimination and 1,2-shifts of an α-hydrogen compete increasingly with 64 and 80.The stereochemistry of ring cleavage and nucleophilic displacement has been explored, using 2-D labels in the case of 17 and 93.Cyclopropanediazonium ions (1) and 41 react stereospecifically, 17 and 44 are moderately stereoselective (ca. 85:15), and 93 is entirely unselective.The data indicate a gradual changeover from concerted to stepwise mechanisms.Appreciable stabilization of the positive charge is required to reach the SN1 extreme.
