Download PDF
Synlett 1991; 1991(5): 339-341
DOI: 10.1055/s-1991-34732
letter
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

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
Further Information

Publication History

Publication Date:
07 March 2002 (online)

  PDF Download  Permissions and Reprints All articles of this category

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).

      >