126456-43-7Relevant articles and documents
Manganese catalyzed asymmetric oxidation of alkanes to optically active ketones bearing asymmetric center at the α- position
Komiya, Naruyoshi,Noji, Satoru,Murahashi, Shun-Ichi
, p. 7921 - 7924 (1998)
Chiral (salen)manganese(III) complex catalyzed oxidation of symmetrical alkanes with iodosylbenzene gives the corresponding optically active ketones (up to 70% ee). The optically active 2-hydroxy-1-indanone (7) thus obtained is a versatile precursor of cis-1-amino-2-indanol (8) which is a key intermediate of chiral auxiliary and anti HIV protease inhibitor (9).
Stereoselective dioxygenase-catalysed benzylic hydroxylation at prochiral methylene groups in the chemoenzymatic synthesis of enantiopure vicinal aminoindanols
Boyd, Derek R.,Sharma, Narain D.,Bowers, Nigel I.,Goodrich, Peter A.,Groocock, Melanie R.,Blacker, A.John,Clarke, David A.,Howard, Tina,Dalton, Howard
, p. 1559 - 1562 (1996)
Enantiopure benzylic alcohols containing two stereogenic centres in a cis- relationship result from stereoselective monohydroxylation of achiral 2- substituted indans in cultures of Pseudomonas putida UV4 and are used in the chemoenzymatic synthesis of both cis- and trans-aminoindanol enantiomers.
Lipase-mediated resolution of inden-1-ol
Takahashi,Koike,Ogasawara
, p. 1585 - 1587 (1995)
Optically pure inden-1-ol has been obtained efficiently in both enantiomeric forms via kinetic deacylation of racemic 1-acetoxyindene using lipase PS.
A practical synthesis of (1S,2R)-1-amino-2-indanol, a key component of an HIV protease inhibitor, indinavir
Kajiro, Hiroshi,Mitamura, Shuichi,Mori, Atsunori,Hiyama, Tamejiro
, p. 1093 - 1100 (1999)
A synthesis of (1S,2R)-1-amino-2-indanol (1), a key component of an HIV protease inhibitor, was accomplished through (R)-2-hydroxy-1-indanone ((R)- 3), which was prepared by an intramolecular Friedel-Crafts acylation of (R)2- acetoxy-3-phenylpropanoic acid readily available from D-(R)-phenylalanine. Alternatively, (R)-3 was obtained by an enzymatic resolution of (±)-2- acetoxy-1-indanone. Ketone (R)-3 was convened into 1 through an oxime formation and diastereoselective hydrogenation.
Efficient diastereoselective synthesis of cis-2-amino-1-indanol derivatives and cis- and trans-1-amino-2-indanol via Pd-catalyzed hydrogenation
Nguyen, Thi Ha,Ma, Eunsook
supporting information, p. 3717 - 3728 (2021/11/01)
(±)-cis-2-amino-1-indanol was diastereoselectively synthesized from 1,2-indanedion-2-oxime in ethanol at 25 °C under 10% Pd/C-catalyzed hydrogenation conditions. Under the same hydrogenation condition, 1,2-indanedion-2-oxime and their derivatives having one and/or two electron-donating groups in aliphatic or aromatic part of indanyl ring were diastereoselectively reduced to racemic cis-2-amino-1-indanol derivatives. From 1,2-indanedion-1-oxime, (±)-trans-1-amino-2-indanol was obtained in ethanol at 25 °C over a 10% Pd/BaSO4 catalyst. In contrast, the 10% Pd/BaSO4-catalyzed hydrogenation reaction in ethanol at 45 °C afforded cis-1-hydroxyamino-2-indanol from 1,2-indanedion-1-oxime, followed by reduction to form (±)-cis-1-amino-2-indanol. The diastereoselectivity of β-aminoindanols was dependent on the Pd catalyst, reaction temperature, and pH of the reaction medium.
Site-Specific C(sp3)–H Aminations of Imidates and Amidines Enabled by Covalently Tethered Distonic Radical Anions
Fang, Yuanding,Fu, Kang,Shi, Lei,Zhao, Rong,Zhou, Jia
, p. 20682 - 20690 (2020/09/07)
The utilization of N-centered radicals to synthesize nitrogen-containing compounds has attracted considerable attention recently, due to their powerful reactivities and the concomitant construction of C?N bonds. However, the generation and control of N-centered radicals remain particularly challenging. We report a tethering strategy using SOMO-HOMO-converted distonic radical anions for the site-specific aminations of imidates and amidines with aid of the non-covalent interaction. This reaction features a remarkably broad substrate scope and also enables the late-stage functionalization of bioactive molecules. Furthermore, the reaction mechanism is thoroughly investigated through kinetic studies, Raman spectroscopy, electron paramagnetic resonance spectroscopy, and density functional theory calculations, revealing that the aminations likely involve direct homolytic cleavage of N?H bonds and subsequently controllable 1,5 or 1,6 hydrogen atom transfer.