A Practical and Scaleable Synthesis of 1 R, 5 S-Bicyclo [3.1. 0] hexan-2-one: The Development of a Catalytic Lithium 2, 2, 6, 6-Tetramethylpiperidide (LTMP) Mediated …

AD Alorati, MM Bio, KMJ Brands, E Cleator…

Index: Alorati, Anthony D.; Bio, Matthew M.; Brands, Karel M. J.; Cleator, Ed; Davies, Antony J.; Wilson, Robert D.; Wise, Chris S. Organic Process Research and Development, 2007 , vol. 11, # 3 p. 637 - 641

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Citation Number: 8

Abstract

An efficient synthesis of 1 R, 5 S-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.