Know More
Weblinks http://www.organic-chemistry.org/synthesis/N1H/reductionsnitrocompounds.shtm https://en.wikipedia.org/wiki/Reduction_of_nitro_compounds http://www.organic-chemistry.org/synthesis/C1N/amines/reductiveamination.shtm
Suggested Readings Overview
Title Organic Synthesis: The Disconnection Approach
CHEMISTRY Paper No. 14: Organic Chemistry –IV (Advance Organic Synthesis and Supramolecular Chemistry and carbocyclic rings) Module No. 10: Disconnection approach for amines and related compounds
Authors Stuart Warren, Paul Wyatt
Edition 2
Publisher John Wiley & Sons, 2011
ISBN 1119965535, 9781119965534
Title March's Advanced Organic Chemistry: Reactions, Mechanisms, and Structure March's Advanced Organic Chemistry
Author Michael B. Smith
Edition 7, illustrated
Publisher Wiley, 2013
ISBN 0470462590, 9780470462591
CHEMISTRY Paper No. 14: Organic Chemistry –IV (Advance Organic Synthesis and Supramolecular Chemistry and carbocyclic rings) Module No. 10: Disconnection approach for amines and related compounds
Title The logic of chemical synthesis
Author E.J. Corey
Publisher Рипол Классик
ISBN 5885010811, 9785885010818
Glossary
D
Disconnection- a retrosynthetic step involving the breaking of a bond to form two (or more) synthons.
R
Retrosynthetic analysis- is a technique for solving problems in the planning of organic syntheses. This is achieved by transforming a target molecule into simpler precursor structures without assumptions regarding starting materials. Each precursor material is examined using the same method.
CHEMISTRY Paper No. 14: Organic Chemistry –IV (Advance Organic Synthesis and Supramolecular Chemistry and carbocyclic rings) Module No. 10: Disconnection approach for amines and related compounds
Time-Lines
Timelines Image Description
1921A.D. A classic named reaction is the Mignonac reaction (1921) involving reaction of a ketone with ammonia over a nickel catalyst for example in a synthesis of 1- phenylethylamine starting from acetophenone.
Fate of reactants during reductive amination
Description
In this organic reaction, the amine first reacts with the carbonyl group to form a hemiaminal species, which subsequently loses one molecule of water in a reversible manner by alkylimino-de-oxo-bisubstitution, to form the imine. The equilibrium between aldehyde/ketone and imine can be shifted toward imine formation by removal of the formed water through physical or chemical means. This intermediate imine can then be isolated and reduced with a suitable reducing agent (e.g., sodium borohydride). This method is sometimes called indirect reductive amination.
Imine formation and reduction occur sequentially in one pot. This approach, known as direct reductive amination, employs reducing agents that are more reactive toward
CHEMISTRY Paper No. 14: Organic Chemistry –IV (Advance Organic Synthesis and Supramolecular Chemistry and carbocyclic rings) Module No. 10: Disconnection approach for amines and related compounds
protonated imines than towards the ketone/aldehyde precursors. These hydride reagents also must tolerate moderately acidic conditions. Typical reagents that meet these criteria
include sodium cyanoborohydride (NaBH3CN) and sodium
triacetoxyborohydride (NaBH(OCOCH3)3). This reaction can be performed in an aqueous environment; which casts doubt on the necessity of forming the imine. Possibly the reaction proceeds via reduction of the hemiaminal species.
SOURCE- https://en.wikipedia.org/wiki/Reductive_amination
Research journals
DESCRIPTION Enantioselective Organocatalytic Reductive Amination
R. Ian Storer , Diane E. Carrera , Yike Ni , and David W. C. MacMillan Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125 J. Am. Chem. Soc., 2006, 128 (1), pp 84–86 DOI: 10.1021/ja057222n Publication Date (Web): December 14, 2005 Copyright © 2006 American Chemical Society
CHEMISTRY Paper No. 14: Organic Chemistry –IV (Advance Organic Synthesis and Supramolecular Chemistry and carbocyclic rings) Module No. 10: Disconnection approach for amines and related compounds
SOURCE- http://pubs.acs.org/doi/abs/10.1021/ja057222n
CHEMISTRY Paper No. 14: Organic Chemistry –IV (Advance Organic Synthesis and Supramolecular Chemistry and carbocyclic rings) Module No. 10: Disconnection approach for amines and related compounds