Amino acid mediated intramolecular asymmetric aldol reaction to construct a new chiral bicyclic enedione containing a seven-membered ring: Remarkable inversion …

T Nagamine, K Inomata, Y Endo…

Index: Nagamine, Takashi; Inomata, Kohei; Endo, Yasuyuki; Paquette, Leo A. Journal of Organic Chemistry, 2007 , vol. 72, # 1 p. 123 - 131

Full Text: HTML

Citation Number: 46

Abstract

A detailed study to assess the enantioselectivity of the amino acid mediated intramolecular asymmetric aldol reaction of 1, 3-cycloheptanedione bearing a C-2 methyl substituent has been undertaken. The cyclizations were mediated by a series of l-amino acids in the presence of an acid cocatalyst. Strikingly, the process is characterized by an inversion of enantioselectivity when compared to a similar reaction involving the 1, 3- ...