Functionalization of Csp 3–H bond—Sc (OTf) 3-catalyzed domino 1, 5-hydride shift/cyclization/Friedel–Crafts acylation reaction of benzylidene Meldrum's acids
SJ Mahoney, DT Moon, J Hollinger, E Fillion
Index: Mahoney, Stuart J.; Moon, David T.; Hollinger, Jon; Fillion, Eric Tetrahedron Letters, 2009 , vol. 50, # 33 p. 4706 - 4709
Full Text: HTML
Citation Number: 45
Abstract
Under Sc (OTf) 3 catalysis, benzylidene Meldrum's acids bearing a tethered p- methoxyphenethyl group were observed to undergo a [1, 5]-hydride shift/cyclization at room temperature, representing a mild Csp3–H bond functionalization. The resulting spiro Meldrum's acid intermediates then underwent intramolecular Friedel–Crafts acylation, completing the one-pot, domino reaction. The reported protocol generates the 6-6-5-6 ...
Related Articles:
[Kimura, Tsutomu; Nishimura, Yuka; Ishida, Naoyuki; Momochi, Hitoshi; Yamashita, Hironori; Satoh, Tsuyoshi Tetrahedron Letters, 2013 , vol. 54, # 9 p. 1049 - 1051]
[Satoh, Tsuyoshi; Sakamoto, Tatsuya; Watanabe, Masanori; Takano, Koji Chemical and Pharmaceutical Bulletin, 2003 , vol. 51, # 8 p. 966 - 970]
[Lyapkalo, Ilya M.; Vogel, Michael A. K.; Boltukhina, Ekaterina V.; Vavrik, Jiri Synlett, 2009 , # 4 p. 558 - 561]
Palladium-catalyzed coupling of aryl triflates with organostannanes
[Echavarren,A.M.; Stille,J.K. Journal of the American Chemical Society, 1987 , vol. 109, p. 5478]
[Kumar, Rahul; Verma, Deepti; Mobin, Shaikh M.; Namboothiri, Irishi N. N. Organic Letters, 2012 , vol. 14, # 16 p. 4070 - 4073]