Most of the compounds have physiologically active properties, and their biological properties are often attributed to the heteroatoms contained in their molecules, and most of these heteroatoms also appear in cyclic structures. A Journal, Article, Research Support, N.I.H., Extramural, Research Support, U.S. Gov’t, Non-P.H.S., Journal of the American Chemical Society called Kinetic Resolution via Rh-Catalyzed C-C Activation of Cyclobutanones at Room Temperature, Author is Deng, Lin; Fu, Yue; Lee, Siu Yin; Wang, Chengpeng; Liu, Peng; Dong, Guangbin, which mentions a compound: 16400-32-1, SMILESS is CCC#CCBr, Molecular C5H7Br, Recommanded Product: 1-Bromo-2-pentyne.
Herein we describe the development of a highly selective kinetic resolution of cyclobutanones via a Rh-catalyzed “”cut-and-sew”” reaction with selectivity factor up to 785. This reaction takes place at room temperature with excellent efficiency. Various trans-5,6-fused bicycles and C2-substituted cyclobutanones were obtained with excellent ee’s that can be further used as chiral building blocks. DFT calculations reveal the crucial roles of the DTBM-segphos ligand in stabilizing the rate- and enantioselectivity-determining C-C oxidative addition transition state via favorable ligand-substrate dispersion interactions.
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Reference:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics