Add time:09/03/2019 Source:sciencedirect.com
The synthesis of (M)-trispiro[3.0.0.3.2.2]tridecane [(M)-4], the first hydrocarbon with a helical primary structure of four-membered rings, is described. Key step is the kinetic resolution of a cyclobutanone through reduction with bakers' yeast. As compared to its analogue of three-membered rings, (M)-trispiro[2.0.0.2.1.1]nonane [(M)-1], the specific rotation of (M)-4 is cut in three. According to molecular mechanics calculations this could be due to a potential to adopt different conformations, not given in (M)-1, and to the fact, that (M)-4 describes a distinctly shorter section of a helix than (M)-1.
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