681824-29-3Relevant academic research and scientific papers
A practical synthesis of a [2.2.1] bicyclic chiral sulfide for asymmetric transformations
Aggarwal, Varinder K.,Fang, Guangyu,Kokotos, Christoforos G.,Richardson, Jeffery,Unthank, Matthew G.
, p. 11297 - 11303 (2006)
A substantially improved synthesis of synthetically useful chiral sulfide 1 is described. Starting from (+)-10-camphorsulfonic acid, the chiral sulfide was synthesised on large scale in five steps and 56% overall yield. Significant improvements include the use of Bu3P in place of Ph3P for the reduction of the chlorosulfonyl group to the thiol, allowing removal of phosphine oxide by aqueous extraction and improvements in the photochemistry using either a modified batch reactor or a single pass continuous flow reactor.
NaOH-Catalyzed Thiolysis of α,β-Epoxyketones in Water. A Key Step in the Synthesis of Target Molecules Starting from α,β -Unsaturated Ketones
Fringuelli, Francesco,Pizzo, Ferdinando,Vaccaro, Luigi
, p. 2315 - 2321 (2007/10/03)
NaOH (0.02-0.3 molar equiv) is an efficient catalyst for the thiolysis reactions of α,β-epoxy ketones with alkyl and aryl thiols in water. Thiolysis of 3,4-epoxyheptan-2-one (1) with thiols 2a-d has been accomplished in mild conditions (30 °C and pH 6 or
Catalytic asymmetric synthesis of epoxides from aldehydes using sulfur ylides with in situ generation of diazocompounds
Aggarwal, Varinder K.,Alonso, Emma,Hynd, George,Lydon, Kevin M.,Palmer, Matthew J.,Porcelloni, Marina,Studley, John R.
, p. 1430 - 1433 (2007/10/03)
A practical, general, and convergent to epoxides with control of the relative and absolute stereochemistry has been achieved by generating the reactive intermediate (the diazo compound) in situ from tosylhydrazone salts (see scheme, PTC = phase-transfer catalyst, Ts = toluene-4-sulfonyl). High yields (58-82%), high d.r. (88:12-98:2), and high ee values (87-94%) have been obtained using a new class of stable chiral sulfides at low catalyst loading (5 mol%) and [Rh2(OAc)4] (0.5 mol%).
