71189-30-5Relevant academic research and scientific papers
Chemoselective Oxidation of Equatorial Alcohols with N-Ligated λ3-Iodanes
Mikhael, Myriam,Adler, Sophia A.,Wengryniuk, Sarah E.
supporting information, p. 5889 - 5893 (2019/08/26)
The site-selective and chemoselective functionalization of alcohols in complex polyols remains a formidable synthetic challenge. Whereas significant advancements have been made in selective derivatization at the oxygen center, chemoselective oxidation to the corresponding carbonyls is less developed. In cyclic systems, whereas the selective oxidation of axial alcohols is well known, a complementary equatorial selective process has not yet been reported. Herein we report the utility of nitrogen-ligated (bis)cationic λ3-iodanes (N-HVIs) for alcohol oxidation and their unprecedented levels of selectivity for the oxidation of equatorial over axial alcohols. The conditions are mild, and the simple pyridine-ligated reagent (Py-HVI) is readily synthesized from commercial PhI(OAc)2 and can be either isolated or generated in situ. Conformational selectivity is demonstrated in both flexible 1,2-substituted cyclohexanols and rigid polyol scaffolds, providing chemists with a novel tool for chemoselective oxidation.
Base-Mediated Meerwein-Ponndorf-Verley Reduction of Aromatic and Heterocyclic Ketones
Boit, Timothy B.,Mehta, Milauni M.,Garg, Neil K.
supporting information, p. 6447 - 6451 (2019/08/20)
An experimental protocol to achieve the Meerwein-Ponndorf-Verley (MPV) reduction of ketones under mildly basic conditions is reported. The transformation is tolerant of a range of ketone substrates, including O- and S-containing heterocycles, is scalable, and shows potential to be used as a platform to access enantioenriched products. These studies provide a general method for achieving the reduction of ketones under mildly basic conditions and offer an alternative protocol to more well-known Al-based MPV reduction conditions.
Chiral spiroaminoborate ester as a highly enantioselective and efficient catalyst for the borane reduction of furyl, thiophene, chroman, and thiochroman-containing ketones
Stepanenko, Viatcheslav,De Jesus, Melvin,Correa, Wildeliz,Bermudez, Lorianne,Vazquez, Cindybeth,Guzman, Irisbel,Ortiz-Marciales, Margarita
experimental part, p. 2659 - 2665 (2010/04/29)
Prochiral heteroaryl ketones containing furan, thiophene, chroman, and thiochroman moieties were successfully reduced in the presence of 1-10 mol % of spiroaminoborate ester 1 with different borane sources to afford non-racemic alcohols in up to 99% ee. In addition, modest enantioselectivity, around 80% ee, was achieved in the reduction of linear α,β-unsaturated heteroaryl ketones.
Synthesis of multi-substituted benzothiophenes: An application of Alder- Rickert reaction
Labadie, Sharada S.
, p. 2531 - 2539 (2007/10/03)
A short synthesis of multi-substituted benzothiophenes using the Alder- Rickert reaction is described.
Antiglaucoma thieno-thiopyran and thieno-thiepin sulfonamide derivatives, compositions, and method of use thereof
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, (2008/06/13)
Aromatic sulfonamides with a saturated heterocycle fused thereto are carbonic anhydrase inhibitors useful in the treatment of elevated intraocular pressure.
