15963-37-8Relevant articles and documents
Retention of Configuration in Oxidation of a Chiral Boronic Acid by the Flavoenzyme Cyclohexanone Oxygenase
Latham, John A.,Walsh, Christopher
, p. 527 - 528 (1986)
The first study of flavoenzyme oxygenation of chiral boronic acids has been carried out and found to occur with retention of configuration at the migrating carbon centre; this is analogous to the migration found in peroxide-mediated oxidations.
(+)- and (-)-myrtanylborane. Solid and Stable Monoalkylboranes for Asymmetric Hydroboration
Richter, Renaud Kiesgen de,Bonato, Marc,Follet, Michel,Kamenka, Jean-Marc
, p. 2855 - 2860 (1990)
Both (+)- and (-)-myrtenyldithiane were independently prepared from commercially available chiral precursors and were easily, and in one step, converted by means of borane complexes into solid and stable chiral monoalkylboranes: (+)- and (-)-2-(1,3-dithianyl)myrtanylborane (MDBH2).These new chiral reagents, when tested on representative classes of olefins, present a reactivity profile similar to IpcBH2: they achieve the asymmetric hydroboration of trisubstituted double bonds with high asymmetric induction.Reduction of asymmetric prochiral ketones with MDBH2 achieves high diastereoselectivity but low enantioselectivity.The likely intramolecular stabilization of MDBH2 not only accounts for the easy access to monoalkylboranes but also for its remarkable physical properties, whereas its efficiency in asymmetric hydroboration is at the same level as that of similar reagents.
Direct Asymmetric Hydrogenation and Dynamic Kinetic Resolution of Aryl Ketones Catalyzed by an Iridium-NHC Exhibiting High Enantio- and Diastereoselectivity
Ayya Swamy P, Chinna,Varenikov, Andrii,de Ruiter, Graham
supporting information, p. 2333 - 2337 (2020/02/11)
A chiral iridium carbene-oxazoline catalyst is reported that is able to directly and efficiently hydrogenate a wide variety of ketones in excellent yields and good enantioselectivity (up to 93 % ee). Moreover, when using racemic α-substituted ketones, excellent diastereoselectivities were obtained (dr 99:1) by dynamic kinetic resolution of the in situ formed enolate. Overall, the herein described hydrogenation occurs under ambient conditions using low hydrogen pressures, providing a direct and atom efficient method towards chiral secondary alcohols.
Catalytic carbonyl hydrosilylations: Via a titanocene borohydride-PMHS reagent system
Fianu, Godfred D.,Schipper, Kyle C.,Flowers, Robert A.
, p. 3469 - 3473 (2017/08/21)
Reduction of a wide range of aldehydes and ketones with catalytic amounts of titanocene borohydride in concert with a stoichiometric poly(methylhydrosiloxane) (PMHS) reductant is reported. Preliminary mechanistic studies demonstrate that the reaction is mediated by a reactive titanocene(iii) complex, whose oxidation state remains constant throughout the reaction.
