A Practical and Scaleable Synthesis of 1<i>R</i>,5<i>S</i>-Bicyclo[3.1.0]hexan-2-one: The Development of a Catalytic Lithium 2,2,6,6-Tetramethylpiperidide (LTMP) Mediated Intramolecular Cyclopropanation of (<i>R</i>)-1,2-Epoxyhex-5-ene
作者:Anthony D. Alorati、Matthew M. Bio、Karel M. J. Brands、Ed Cleator、Antony J. Davies、Robert D. Wilson、Chris S. Wise
DOI:10.1021/op700042w
日期:2007.5.1
An efficient synthesis of 1R,5S-bicyclo[ 3.1.0] hexan-2-one from (R)-1,2-epoxyhex-5-ene is described. Development of a catalytic intramolecular cyclopropanation of (R)-1,2-epoxyhex-5-ene gives the key homochiral bicycle[ 3.1.0] hexan-1-ol, which is then oxidized to the desired ketone. This process has been successfully demonstrated on a multi-kilogram scale.