Mild and efficient desymmetrization of diynes via hydroamination: application to the synthesis of (+/-)-monomorine I.
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 (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.
Iska
Vijaya Bhaskara Reddy
VB
Department of Chemistry and Biochemistry, University of Notre Dame, 251 Nieuwland Science Hall, Notre Dame, Indiana 46556, USA.
Verdolino
Vincenzo
V
Wiest
Olaf
O
Helquist
Paul
P
D000586:Amination; D002384:Catalysis; D053280:Diynes / Q000737:chemistry*; D007212:Indolizines / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D015394:Molecular Structure; D011758:Pyrroles / Q000737:chemistry; D012834:Silver / Q000737:chemistry; D013237:Stereoisomerism
D053280:Diynes; D007212:Indolizines; D011758:Pyrroles; C110223:indolizidine-195B; C013231:pyrroline; D012834:Silver