942-81-4Relevant articles and documents
Regio- and stereoselective synthesis of chiral nitrilolactones using Baeyer–Villiger monooxygenases
Fink, Michael J.,Snajdrova, Radka,Winninger, Alexander,Mihovilovic, Marko D.
, p. 7241 - 7248 (2016/10/26)
This work describes the regio- and enantioselective synthesis of nitrile-containing chiral lactones from easily accessible ketone precursors using Baeyer–Villiger monooxygenases. These biocatalysts controlled the distribution of regioisomers much more tightly than commonly used stoichiometric reagents, additionally with good to excellent optical purity of products. A surprising case of strong stereoelectronic control was also observed. We tested a library of 14 catalysts using five-to eight-membered cyclic ketones with two different tether lengths to the nitrile group. In all but the largest series we found suitable wild-type enzymes for preparative scale synthesis of the target compounds. The diverse possibilities to further functionalize lactones and nitriles make this method interesting for the generation of chiral building blocks.
Synthesis and characterisation of medium-sized ring systems by oxidative cleavage. Part 2: Insights from the study of ring expanded analogues
Lebl, Tomas,Lorion, Magali M.,Jones, Alan M.,Philp, Douglas,Westwood, Nicholas J.
experimental part, p. 9694 - 9702 (2011/02/23)
Variable temperature NMR analysis and computational methods have been used to develop a detailed understanding of the 1H NMR spectra of a family of medium-sized ring containing compounds. The family consists of analogues containing 10-, 11- and
THE ?-BARRIER TO ROTATION IN STERICALLY UNHINDERED ENAMINES: CONFORMATIONAL STUDIES BY DYNAMIC NMR, XXXVIII
Lunazzi, Lodovico,Casarini, Daniele,Anderson, J.Edgar
, p. 217 - 221 (2007/10/02)
The ?-barriers to rotation about the enamine (N-Csp2) bond in four pyrrolidinocyclo-n-alkenes (n = 5, 6, 7, 8) have been determined, and are discussed in terms of the steric interactions between the pyrrolidine and cycloalkene rings in the ground state.Distinct barriers were determined for two different conformations of the cyclooctene ring.Barriers were determined in two acyclic N,N-(dialkylamino)cycloalkenes for reference comparison.