Variable Synthesis of Alcohols and Ketones Using the Grignard Method as a Form of MPVO Reaction

Abstract

The unexpected occurrence of ketones 9 and 16 in addition to expected alcohols 5 and 15 in the synthesis of sesquiterpenes salsolenketone 1 and salsolene oxide 2 during Grignard reactions of the corresponding aldehydes with bromoalkenes under air‐ and water‐free conditions by the Meerwein–Ponndorf–Verley–Oppenauer reaction is reported. The product distribution could be influenced by the amounts of aldehyde used.

In Memoriam to Prof. Peter Weyerstahl.

Keywords:

• Grignard reaction
• hydride transfer
• magesium alcoholates
• Meerwein–Ponndorf–Verley–Oppenauer reaction

Notes

In Memoriam to Prof. Peter Weyerstahl.