Lewis acid-mediated ring opening of propargylic epoxides: A stereospecific synthesis of 1,2-disubstituted homopropargylic alcohols.
โ Scribed by Nicolas Bernard; Fabrice Chemla; Jean F. Normant
- Book ID
- 108386991
- Publisher
- Elsevier Science
- Year
- 1998
- Tongue
- French
- Weight
- 152 KB
- Volume
- 39
- Category
- Article
- ISSN
- 0040-4039
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๐ SIMILAR VOLUMES
Bromoallenols derived from propargylic epoxides are transformed in two steps and in a stereospecific fashion into 1,2-disubstituted homopropargylic protected alcohols with Grignard reagents with or without copper salts.
A Stereospecific Synthesis of 1,2-Disubstituted Homopropargylic Protected Alcohols from Bromoallenols. -Bromoallenols [cf. (I)] or the related ethers [cf. (V)] undergo a stereospecific reaction with organocopper or Grignard reagents providing 1,2-disubstituted derivatives (III) and (VII).
AlPW 12 O 40 as a recyclable Lewis acid and stable solid compound was introduced for efficient ring opening of different epoxides with thiols, acetic acid, and primary, secondary, and tertiary alcohols. These processes were carried out at room temperature with high regio-and stereoselectivity.