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A stereospecific synthesis of 1,2-disubstituted homopropargylic protected alcohols from bromoallenols

โœ Scribed by Nicolas Bernard; Fabrice Chemla; Jean F. Normant

Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
187 KB
Volume
40
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

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.

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โœ Nicolas Bernard; Fabrice Chemla; Jean F. Normant ๐Ÿ“‚ Article ๐Ÿ“… 2010 ๐Ÿ› John Wiley and Sons โš– 28 KB ๐Ÿ‘ 1 views

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).

A New Diastereodivergent Synthesis of 1,
A New Diastereodivergent Synthesis of 1,2-Disubstituted Homopropargylic Alcohols
โœ Fabrice Chemla; Nicolas Bernard; Jean Normant ๐Ÿ“‚ Article ๐Ÿ“… 1999 ๐Ÿ› John Wiley and Sons ๐ŸŒ English โš– 349 KB ๐Ÿ‘ 2 views

Disubstituted homopropargylic alcohols can be prepared inversion through the intermediate formation of a bromoallenol moiety. in a diastereodivergent fashion starting from propargylic epoxides by BF 3 -catalysed direct ring-opening or by double served. Thus disubstituted anti homopropargylic alcohol