α-Aminoallylation of Aldehydes with Ammonia: Stereoselective Synthesis of Homoallylic Primary Amines
- 22 May 2004
- journal article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 126 (23) , 7182-7183
- https://doi.org/10.1021/ja049689o
Abstract
Three-component reactions of aldehydes, ammonia, and allylboronates were found to provide homoallylic primary amines in high yields with high chemo- and stereoselectivities. A two-step, one-pot, stereoselective synthesis of an uncommon alpha-amino acid, alloisoleucine, was achieved utilizing this reaction.Keywords
This publication has 11 references indexed in Scilit:
- New Stereodivergent Approach to 3-Amino-2,3,6-trideoxysugars. Enantioselective Synthesis of Daunosamine, Ristosamine, Acosamine, and Epi-daunosamineOrganic Letters, 2003
- Multicomponent Reactions with IsocyanidesPublished by Wiley ,2000
- Practical Synthesis of (+)-AlloisoleucineSynthetic Communications, 2000
- The Critical Importance of Water in the Asymmetric Allylboration ofN-Trimethylsilylbenzaldimines withB-AllyldiisopinocampheylboraneAngewandte Chemie International Edition in English, 1999
- A New and Practical Synthesis of α-Amino Acids from Alkenyl Boronic AcidsJournal of the American Chemical Society, 1997
- Selective reactions using allylic metalsChemical Reviews, 1993
- Stereoselective Synthesis of Alcohols, XXXII. Synthesis of the Prelog‐Djerassi Aldehyde and of a C‐1/C‐9 Segment of 6‐DeoxyerythronolideEuropean Journal of Organic Chemistry, 1989
- Stereochemistry of the reactions of substituted allylboronates with chiral aldehydes. Factors influencing aldehyde diastereofacial selectivityJournal of the American Chemical Society, 1986
- Stereochemistry of the reactions of pinacol allylboronate with two α,β-dialkoxyaldehydesTetrahedron Letters, 1985
- Ueber die künstliche Bildung der Milchsäure und einen neuen, dem Glycocoll homologen Körper;European Journal of Organic Chemistry, 1850