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 | Health & Environmental Research Online (HERO)

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Citation
Tags

HERO ID

7271908

Reference Type

Journal Article

Title

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

Author(s)

Alorati, AD; Bio, MM; Brands, KMJ; Cleator, Ed; Davies, AJ; Wilson, RD; Wise, CS; ,

Year

2007

Is Peer Reviewed?

Journal

Organic Process Research and Development
ISSN: 1083-6160

Publisher

AMER CHEMICAL SOC

Location

WASHINGTON

Page Numbers

637-641

DOI

10.1021/op700042w

Web of Science Id

WOS:000246570400049

Abstract

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.