en
Scientific article
English

Chiral aminal templates: Diastereoselective addition to hydrazones; an asymmetric synthesis of α-amino aldehydes

Published inSynthesis, no. 8, p. 1038-1050
Publication date1995
Abstract

The monohydrazone of glyoxal may be derivatized into a chiral aminal with diamine 7. The resulting chiral reagent 13 reacts with complete diastereocontrol with organolithium reagents in THF. This sterically controlled reaction may be altered to chelation control by using Grignard reagents in toluene, affording the opposite diastereomer in excellent de. The N-N bond of the hydrazine functionality is then cleaved with Raney nickel, assisted by ultrasound. After protection of the resulting primary amino functionality, the aminal is hydrolyzed to afford the desired a-amino aldehydes without epimerization. The same reaction sequence, without cleavage of the N-N bond, affords an a-hydrazino aldehyde.

Keywords
  • glyoxal
  • chiral aminals
  • hydrazones
  • chiral a-amino aldehydes
Affiliation Not a UNIGE publication
Citation (ISO format)
ALEXAKIS, Alexandre et al. Chiral aminal templates: Diastereoselective addition to hydrazones; an asymmetric synthesis of α-amino aldehydes. In: Synthesis, 1995, n° 8, p. 1038–1050. doi: 10.1055/s-1995-4042
Main files (1)
Article (Published version)
accessLevelRestricted
Identifiers
ISSN of the journal0039-7881
581views
0downloads

Technical informations

Creation06/21/2010 2:44:15 PM
First validation06/21/2010 2:44:15 PM
Update time03/14/2023 3:48:18 PM
Status update03/14/2023 3:48:18 PM
Last indexation01/15/2024 8:28:11 PM
All rights reserved by Archive ouverte UNIGE and the University of GenevaunigeBlack