Asymmetric synthesis of 1,2-amino alcohols using (S)-indoline chiral auxiliary

Chirality. 2000 Jun;12(5-6):404-7. doi: 10.1002/(SICI)1520-636X(2000)12:5/6<404::AID-CHIR19>3.0.CO;2-2.

Abstract

Chiral hydrazones 1 reacted with aryl- or alkyl-lithiums at -78 degrees C in a short reaction time, within 10 min, to afford arylated or alkylated chiral hydrazines 3 with extremely high diastereoselectivity (up to >99% de) and high chemical yields. The hydrazines are readily converted to chiral amino alcohols 4.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Alcohols / chemical synthesis*
  • Amino Alcohols / chemistry*
  • Chemistry / methods*
  • Chromatography, High Pressure Liquid
  • Indoles / chemistry
  • Lithium / chemistry
  • Models, Chemical
  • Stereoisomerism

Substances

  • Amino Alcohols
  • Indoles
  • indoline
  • Lithium