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Mild and Efficient Desymmetrization of Diynes via Hydroamination: Application to the Synthesis of (±)-Monomorine I

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journal contribution
posted on 19.02.2010, 00:00 by Vijaya Bhaskara Reddy Iska, Vincenzo Verdolino, Olaf Wiest, Paul Helquist
An efficient silver-catalyzed desymmetrization of amino diynes via hydroamination is reported. A variety of functionalized 1-pyrroline derivatives were synthesized in 73% to 88% isolated yields (>98% by 1H NMR in some cases). The usefulness of this mild hydroamination method was further shown by the desymmetrization of unprotected tert-hydroxy diynes. Structures of two transition states have been studied computationally. An application of this method was demonstrated by a short and efficient synthesis of (±)-monomorine I.