Journal Article
A practical and scaleable synthesis of 1R,5S-bicyclo[3.1.0]hexan-2-one: The development of a catalytic lithium 2,2,6,6-tetramethylpiperidide (LTMP) mediated intramolecular cyclopropanation of (R)-1,2-epoxyhex-5-ene
Alorati, AD; Bio, MM; Brands, KMJ; Cleator, Ed; Davies, AJ; Wilson, RD; Wise, CS; ,
Organic Process Research and Development
ISSN: 1083-6160
AMER CHEMICAL SOC
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.