A Mild Multistep Conversion of N-Protected alpha-Amino Acids into N-Protected beta(3)-Amino Acids Utilizing the Nef Reaction
- Author(s)
- Sleebs, BE; Nguyen, NH; Hughes, AB;
- Details
- Publication Year 2013-04,Volume 24,Issue #6,Page 747-751
- Journal Title
- SYNLETT
- Publication Type
- Journal Article
- Abstract
- Current methods of homologation of alpha-amino acids to beta-amino acids have limitations. To overcome these shortfalls the Nef reaction has been utilized in the multistep synthesis of beta(3)-amino acids from alpha-amino acids. In this approach, N-protected amino aldehydes, easily accessed from alpha-amino acids, were transformed into the N-protected.gamma-amino nitroalkanes. The Nef reaction was then used to smoothly convert the nitroalkanes into the corresponding N-protected beta(3)-amino acids without notable racemization.
- Publisher
- GEORG THIEME VERLAG KG
- Keywords
- amino acids ; amino alcohols ; amino aldehydes ; nucleophilic addition ; enantioselectivity
- Research Division(s)
- Chemical Biology
- Publisher's Version
- https://doi.org/10.1055/s-0032-1318344
- Terms of Use/Rights Notice
- © 2012 Georg Thieme Verlag KG
Creation Date: 2013-04-01 12:00:00
Last Modified: 2014-12-11 02:33:39