Journal of the American Chemical Society

Chiral leaving groups induce asymmetry in syntheses of binaphthyls in nucleophilic aromatic substitution reactions

JM Wilson, DJ Cram

Index: Wilson, Janet M.; Cram, Donald J. Journal of the American Chemical Society, 1982 , vol. 104, # 3 p. 881 - 884

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Citation Number: 80

Abstract

in I-menthol-sodium I-menthoxide (90 OC, 3.5 h) or in a-fencholsodium a-fenchoxide (90 OC, 6 h), respectively. Ethers 1-5l1 were synthesized from a-bromo-j3- oxazolinonaphthalene and the corresponding sodium alkoxide (NaH+ ROH) in DMF at 50 OC in 87%(5 h), 67%(20 h), 45%(15 h), 83%(15 h), and 73%(3 h) yields, respectively. The nucleophiles that gave normal products were a-naphthyllithium (6) and j3-methoxy- ...