Utilization of sulfur-containing leaving group. 7. Highly selective nonenzymic chiral induction into 3-methylglutaric acid and cis-4-cyclohexen-1, 2-ylenebis (acetic acid) …
Y Nagao, T Ikeda, T Inoue, M Yagi…
Index: Nagao, Yoshimitsu; Ikeda, Takao; Inoue, Takehisa; Yagi, Masahiro; Shiro, Motoo; Fujita, Eiichi Journal of Organic Chemistry, 1985 , vol. 50, # 21 p. 4072 - 4080
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Citation Number: 39
Abstract
Diamide 8, prepared by treatment of 3-methylglutaric acid (1) with 4 (R)-MCTT (5) in the presence of DCC in pyridine, was subjected to aminolysis with 1 equiv of piperidine in CH2C12 at-30 “C to give a mixture of diastereomers 9a and 10a in a 88: 12 ratio. Compound 9a, separated by silica gel column chromatography, was treated with various nucleophiles to give optically pure bifunctional synthons lla-k in high yields. Highly selective chiral ...
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