Details

Autor(en) / Beteiligte

• Janicki, Slawomir Z
• Fairgrieve, Jennifer M
• Petillo, Peter A

Titel

A Facile, General Approach to the Synthesis of Electrophilic Acetone Equivalents

Ist Teil von

• Journal of organic chemistry, 1998-05, Vol.63 (11), p.3694-3700

Ort / Verlag

American Chemical Society

Erscheinungsjahr

1998

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• The facile, high-yielding, yet general synthesis of electrophilic chloroacetone equivalents 11a−f is described. The enol ethers are assembled in three steps starting with trichloride 29 in overall yields of 57−93%. Nucleophilic displacement of the chloromethyl chlorine with a range of organometallic reagents generates dichlorides 30 in yields of 58−99%, which can be dehydrohalogenated with t-BuOK/THF in yields of 87−99% to produce enol ethers 31. Conversion of the allyl chlorides 31 to the corresponding allyl iodides 11 with 72−99% yield completes the synthetic sequence. The entire sequence can be performed in less than 48 h on a >50 mmol scale.