42361-59-1Relevant academic research and scientific papers
Convergent Evolution of Diastereomeric Mixtures of 5-Methoxy-pentylzirconocenes toward Trans-1,2-substituted Cyclopentanes
Coelho, Aurélien,Machado-Rodrigues, Carine,Behr, Jean-Bernard,Vasse, Jean-Luc
, p. 772 - 776 (2021)
The access to 1,2- and 1,1,2-substituted trans cyclopentanes via a sequential hydrozirconation/TMSOTf-mediated cyclization applied to 5-methoxypent-1-enes is presented. Involving a transient carbocation, the reaction was shown to be diastereo-convergent. Possibly performed in a nonracemic version, the reaction proved compatible with a range of functional groups affording a large panel of cyclopentanes.
Fluorine-directed diastereoselective iodocyclizations
Tredwell, Matthew,Luft, Jennifer A. R.,Schuler, Marie,Tenza, Kenny,Houk, Kendall N.,Gouverneur, Veronique
, p. 357 - 360 (2008/09/19)
(Chemical Equation Presented) An inside job: β-Fluorinated lactones and tetrahydrofurans are synthesized by iodocyclization of various allylic fluorides. The fluorine substituent acts as a highly efficient syn-stereodirecting group for the ring closure. T
Remarkable electronic and steric effects in the nitrile biotransformations for the preparation of enantiopure functionalized carboxylic acids and amides: Implication for an unsaturated carbon-carbon bond binding domain of the amidase
Gao, Ming,Wang, De-Xian,Zheng, Qi-Yu,Huang, Zhi-Tang,Wang, Mei-Xiang
, p. 6060 - 6066 (2008/02/10)
(Chemical Equation Presented) Biotransformations of various functionalized racemic nitriles catalyzed by Rhodococcus erythropolis AJ270, a nitrile hydratase/amidase-containing microbial whole-cell catalyst, were studied. While the nitrile hydratase exhibi
Asymmetric Induction in the Claisen Rearrangement of N-Allylketene N,O-Acetals
Kurth, Mark J.,Decker, Owen H. W.,Hope, Hakon,Yanuck, Michael D.
, p. 443 - 448 (2007/10/02)
Asymmetric C-C bond formation via the diastereoselective aza-Claisen rearrangement of N-allylketene N,O-acetal 1 is described.Diastereoselection noted for rearrangement 1->2 ranges from 84percent to 96percent and is a consequence of complete (Z)-N,O-acetal olefin selectivity in 1, high Cα-si-face selectivity in the rearrangement of 1 to 2, and the absence of Cα epimerization in oxazoline 2.Experiments which establish the steric bulk of the C4 appendage as a particularly important variable are also reported.Acid-catalyzed hydrolysis of rearranged oxazoline 2 completes an efficient, enantioselective synthesis of 2-substituted pent-4-enoic acid 4 and regenerates for recycling the chiral auxiliary reagent 3, initially prepared from inexpensive α-amino acids.
