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ChemInform Abstract: An in situ Procedure for Catalytic, Enantioselective Acetate Aldol Addition. Application to the Synthesis of (R)-(-)-Epinephrine.

✍ Scribed by R. A. SINGER; E. M. CARREIRA

Publisher: John Wiley and Sons
Year: 2010
Weight: 34 KB
Volume: 28
Category: Article
ISSN: 0931-7597
DOI: 10.1002/chin.199725079

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✦ Synopsis

An in situ Procedure for Catalytic, Enantioselective Acetate Aldol Addition. Application to the Synthesis of (R)-(-)-Epinephrine.

-In order to simplify the generation of the catalyst of the title reaction the formed isopropanol is fixed as the corresponding trimethylsilylether to circumvent the azeotropic removal. This silylether does not influence the formation of the aldols such as (III) , (V), and (VII) with respect to yield or e.e.-values. This methodology is applied to an efficient synthesis of (-)-epinephrine (X) in 45% overall yield. It is noteworthy that the addition of molecular sieves in the catalyst generation procedure does not give an adequate solution. -(SINGER,

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