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Synlett 1991; 1991(5): 339-341
DOI: 10.1055/s-1991-34732
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Diastereodivergent Synthesis of Amino Alcohol Derivatives from N-Acyl-N,O-acetals. SN2-Type Displacement with Organocopper-Boron Trifluoride Reagents

Yoshinori Yamamoto* , Hisashi Sato, Jun-ichi Yamada
  • *Department of Chemistry, Faculty of Science, Tohoku University, Sendai 980, Japan
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Publication Date:
07 March 2002 (online)

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The reaction of the 5-membered α-methoxycarbamate 8 (5-hexyl-4-methoxy-3-methyl-2-oxazolidinone) with organocopper-boron trifluoride reagents gave the SN2-type displacement product predominantly, whereas the reaction with allyl-trimethylsilane, allyltributyltin, and 9-allyl-9-borabicyclo[3.3.1]-nonane afforded the SN1-type product preferentially. The similar stereodivergent reaction took place with 6-membered α-ethoxycarbamate 12 (4-ethoxy-6-heptyl-3-methyl-1,3-oxazan-2-one).