144461-87-0Relevant articles and documents
Photocatalytic Reductive Radical-Polar Crossover for a Base-Free Corey–Seebach Reaction
Crespi, Stefano,Donabauer, Karsten,K?nig, Burkhard,Murugesan, Kathiravan,Rozman, Ur?a
supporting information, p. 12945 - 12950 (2020/09/23)
A metal-free generation of carbanion nucleophiles is of prime importance in organic synthesis. Herein we report a photocatalytic approach to the Corey–Seebach reaction. The presented method operates under mild redox-neutral and base-free conditions giving the desired product with high functional group tolerance. The reaction is enabled by the combination of photo- and hydrogen atom transfer (HAT) catalysis. This catalytic merger allows a C?H to carbanion activation by the abstraction of a hydrogen atom followed by radical reduction. The generated nucleophilic intermediate is then capable of adding to carbonyl electrophiles. The obtained dithiane can be easily converted to the valuable α-hydroxy carbonyl in a subsequent step. The proposed reaction mechanism is supported by emission quenching, radical–radical homocoupling and deuterium labeling studies as well as by calculated redox-potentials and bond strengths.
Electrophilic amination of ketone enolates mediated by the DiTOX asymmetric building block: Enantioselective formal synthesis of α-aminoacids
Bulman Page, Philip C.,McKenzie, Michael J.,Allin, Steven M.,Buckle, Derek R.
, p. 9683 - 9695 (2007/10/03)
Diastereoselective electrophilic amination of enolates derived from 2-acyl-1,3-dithiane 1-oxides is used as the key step for an enantioselective synthesis of two α-hydrazido carboxylic acids, well-known precursors of α-amino acids. (C) 2000 Elsevier Science Ltd.
Enantioselective preparation of 2-substituted-1,3-dithiane 1-oxides using modified Sharpless sulphoxidation procedures
Page, Philip C. Bulman,Wilkes, Robin D.,Namwindwa, Ernest S.,Witty, Michael J.
, p. 2125 - 2154 (2007/10/03)
Enantioselective sulphoxidation of a wide range of 2-substituted-1,3-diathianes has been carried out using modified Sharpless conditions to furnish the corresponding sulphoxides in optically enriched form. Deacylation of 2-acyl-1,3-dithiane 1-oxide deriva