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

作者：Iska Vijaya Bhaskara Reddy; Verdolino Vincenzo; Wiest Olaf^*; Helquist Paul

来源：Journal of Organic Chemistry, 2010, 75(4): 1325-1328.

DOI：10.1021/jo902674j

An efficient silver-catalyzed desymmetrization of amino diynes via hydroamination is reported. A variety of functionalized I-pyrroline derivatives were synthesized in 73% to 88% isolated yields (>98% by (1)H 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.

• 出版日期2010-2-19