Enantioselective Protonation of a Simple Enol: Aminoalcohol-Catalyzed Ketonization of a Photochemically Produced 2-Methylinden-3-ol

Enantioselective Protonation of a Simple Enol: Aminoalcohol-Catalyzed Ketonization of a Photochemically Produced 2-Methylinden-3-ol

The enol 2, produced by a Norrish type II photoelimination from 1, is protonated enantioselectively to ketone 3 in the presence of (–)‐ephedrine. Best optical yields are obtained at 0oC using small amounts of the chiral aminoalcohol. There is still wide scope for optimization.

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Veröffentlicht in:Angewandte Chemie International Edition 1991-04, Vol.30 (4), p.416-418
Hauptverfasser: Henin, Franpise, Muzart, Jacques, Pete, Jean-Pierre, M'boungou-M'passi, Anastase, Rau, Hermann
Format: Artikel
Sprache:eng
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Zusammenfassung:The enol 2, produced by a Norrish type II photoelimination from 1, is protonated enantioselectively to ketone 3 in the presence of (–)‐ephedrine. Best optical yields are obtained at 0oC using small amounts of the chiral aminoalcohol. There is still wide scope for optimization.
ISSN:0570-0833
1521-3773
DOI:10.1002/anie.199104161