1576-84-7Relevant articles and documents
Synthesis of L-ascorbic acid derivatives as potential bone remodeling agents taking advantage of the Mitsunobu reaction
Vila?a, Gil,Rubio, Cyril,Susperregui, Jacques,Latxague, Laurent,Déléris, Gérard
, p. 9249 - 9256 (2002)
The synthesis of ascorbic acid derivatives 7a-d is described. Starting from alkenylacetates 1a-d subjected to a hydrosilylation reaction, the resulting hydroxy chloro silanes 3a-d were obtained in high yield. The latter compounds were reacted with potassium phthalimide followed with hydrazine hydrate to give the amino silanols 5a-d. Ascorbic acid was then alkylated on its 3-hydroxy position to give 7a-d by means of a Mitsunobu reaction.
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Foster,D.J.,Tobler,E.
, p. 834 - 837 (1962)
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Developing a Bench-Scale Green Diboration Reaction toward Industrial Application
Farre, Albert,Briggs, Rachel,Pubill-Ulldemolins, Cristina,Bonet, Amadeu
supporting information, p. 4775 - 4782 (2017/10/27)
We report a new methodology for the organocatalytic diboration reaction using inexpensive, sustainable, nontoxic, commercially available halogen salts. This is an educative manuscript for the transformation of laboratory scale reactions into a sustainable approach of appeal to industry.
Iron-Catalyzed Cross-Coupling of Alkenyl Acetates
G?rtner, Dominik,Stein, André Luiz,Grupe, Sabine,Arp, Johannes,Von Wangelin, Axel Jacobi
supporting information, p. 10545 - 10549 (2015/09/02)
Stable C-O linkages are generally unreactive in cross-coupling reactions which mostly employ more electrophilic halides or activated esters (triflates, tosylates). Acetates are cheap and easily accessible electrophiles but have not been used in cross-couplings because the strong C-O bond and high propensity to engage in unwanted acetylation and deprotonation. Reported herein is a selective iron-catalyzed cross-coupling of diverse alkenyl acetates, and it operates under mild reaction conditions (0 C, 2 h) with a ligand-free catalyst (1-2 mol%). Iron clad: Acetates are underutilized electrophiles in metal-catalyzed cross-coupling reactions because of the strong alkenyl C-O bond and their propensity to engage in unwanted reactions. Combination of a ligand-free low-valent Fe catalyst with nucleophilic organomagnesium reagents, low temperature, and short reaction times results in highly selective cross-couplings with alkenyl acetates.
