Stereospecific 1,2-rearrangement of cyclopropyl group. Synthesis of chiral α-cyclopropyl ketones and α-cyclopropyl aldols

✍ Scribed by Masato Shimazaki; Hisaaki Hara; Keisuke Suzuki

• Publisher: Elsevier Science
• Year: 1989
• Tongue: French
• Weight: 294 KB
• Volume: 30
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)80589-x

✦ Synopsis

Stereospecific 1,2-rearrangement of cyclopropyl group is described as an efficient route to stereo-defined a-cyclopropyl ketones and cr-cyclopropyl aldols.

Acceleration of the reaction by the introduction of trimethylsilyl (TMS) group to the a-position of cyclopropyl group is also noted.

Cyclopropane-containing

compounds are gaining growing interest in view of their specific and potentially useful biological functions such as enzyme inhibitory effectsl) Thus, the synthetic methods