Enantiodifferentiating photocyclodimerization of 2-anthracenecarboxylic acid using a chiral N-(2-hydroxymethyl-4- pyrrolidinyl)benzamide template.
[Structure: see text] Supramolecular enantiodifferentiating photocyclodimerization of 2-anthracenecarboxylic acid (AC) was performed in the presence of (2S,4S)-4-amino-5-chloro-2-methoxy-N-(1-ethyl-2-hydroxymethyl-4-pyrrolidinyl)benzamide (TKS159), and its stereoisomers were employed as chiral templates. The TKS template provides us with a novel hydrogen-bonding and shielding motif for enantioface-selectively binding an AC molecule. Chiral products 2 and 3 were obtained in good enantiomeric excesses (ee's) of 40% and 40%, respectively.
Mizoguchi
Jun-ichi
J
Bio/Fine Chemicals Department, Nagase ChemteX Corporation, 2-2-3 Murotani, Nishi-ku, Kobe 651-2241, Japan.
Kawanami
Yuko
Y
Wada
Takehiko
T
Kodama
Kazuya
K
Anzai
Kinsei
K
Yanagi
Toshiharu
T
Inoue
Yoshihisa
Y