✦ LIBER ✦

An Approach to Catalytic Enantioselective Protonation of Prochiral Lithium Enolates

✍ Scribed by Pierre Riviere; Kenji Koga

Publisher: Elsevier Science
Year: 1997
Tongue: French
Weight: 517 KB
Volume: 38
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(97)01790-5

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✦ Synopsis

Protonationof prochirallithiumenolates(4), preparedfromracemic2substituted-1 -tetralones(2) via their silyl enolethers(3), withexcesssuccinimidein the presenceof lithiumbromideand0.2equivalentof a chiraltetmdentateamine((R)-1)in tolueneat -78'Cgaveopticallyactive2 in upto 83%ee. @1997 Elsevier Science Ltd.

Enantioselective protonationof prochiralenolatesis a promisingmethodforthepreparationof optically activecarbonylcompoundshavinga chiraltertiarycarbonat the a-positionof thecarbonylgroup,becausethis methodmakesit possibleto convertthe racemiccarbonylcompoundsintothe correspondingopticallyactive ones. Sincethe pioneeringworkby Duhamel,3 manyexampleshavebeenreportedto date,4includingcatalytic versionsof this process.5

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