The Journal of Organic Chemistry

Studies in stereochemistry. 47. Asymmetric induction by leaving group in nucleophilic aromatic substitution

JM Wilson, DJ Cram

Index: Wilson, Janet M.; Cram, Donald J. Journal of Organic Chemistry, 1984 , vol. 49, # 25 p. 4930 - 4943

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Citation Number: 80

Abstract

Results Feasibility. To establish feasibility for synthesizing binaphthyl compounds by nucleophilic aromatic substitutions, model reactions of 1 with several naphthyl or- ganometallic reagents were studied. Compound 1 was!!!! oa!! prepared by standard pro~ eduresl~~ J~ from l-methoxy-2-naphthoic acid. ls When treated with 2 or 3 in benzene at 80" C in the presence of Ni (Ph3P) 2C12 catalyst, 16 6 (96%) and 7 (80%) were formed, ...