1-bromo-1-lithioethene: a practical reagent for the efficient preparation of 2-bromo-1-alken-3-ols

Yehor Y Novikov; Paul Sampson

doi:10.1021/ol034594x

1-bromo-1-lithioethene: a practical reagent for the efficient preparation of 2-bromo-1-alken-3-ols

Org Lett. 2003 Jun 26;5(13):2263-6. doi: 10.1021/ol034594x.

Authors

Yehor Y Novikov¹, Paul Sampson

Affiliation

¹ Department of Chemistry, Kent State University, Kent, Ohio 44242, USA. ynoviko1@kent.edu

PMID: 12816424
DOI: 10.1021/ol034594x

Abstract

A reliable preparative-scale synthesis of 1-bromo-1-lithioethene is reported. This reagent undergoes clean 1,2-addition with a range of aldehydes and ketones at -105 degrees C to afford the corresponding 2-bromo-1-alken-3-ols in moderate to excellent yield. Efficient diastereoselective addition to alpha-siloxy and alpha-methylcyclohexanones, as well as protected 3-keto furanose sugars, is achieved in the presence of 10 mol % CeBr(3). The resulting bromoallylic alcohol adducts have considerable potential as synthetic building blocks. [reaction: see text]