98102-92-2Relevant articles and documents
Stereoselective hydrogenation of simple ketones catalyzed by ruthenium(II) complexes
Ohkuma, Takeshi,Ooka, Hirohito,Yamakawa, Masashi,Ikariya, Takao,Noyori, Ryoji
, p. 4872 - 4873 (1996)
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Cytochrome P450 catalyzed oxidative hydroxylation of achiral organic compounds with simultaneous creation of two chirality centers in a single C-H activation step
Roiban, Gheorghe-Doru,Agudo, Ruben,Reetz, Manfred T.
supporting information, p. 8659 - 8663 (2014/08/18)
Regio- and stereoselective oxidative hydroxylation of achiral or chiral organic compounds mediated by synthetic reagents, catalysts, or enzymes generally leads to the formation of one new chiral center that appears in the respective enantiomeric or diastereomeric alcohols. By contrast, when subjecting appropriate achiral compounds to this type of C-H activation, the simultaneous creation of two chiral centers with a defined relative and absolute configuration may result, provided that control of the regio-, diastereo-, and enantioselectivity is ensured. The present study demonstrates that such control is possible by using wild type or mutant forms of the monooxygenase cytochrome P450 BM3 as catalysts in the oxidative hydroxylation of methylcyclohexane and seven other monosubstituted cyclohexane derivatives.
Diastereoselective reduction of cyclohexanones with diisobutylaluminium phenoxides in terms of the isoinversion principle
Meyer-Stork, Markus A.,Haag, Dieter,Scharf, Hans-Dieter
, p. 593 - 595 (2007/10/03)
The diastereoselectivity of the reduction of 2-substituted cyclohexanones 1-6 with 4-substituted diisobutylaluminium phenoxides a-d has been investigated as a function of temperature. The high-temperature region is found to be dominated by hydride transfer, which is controlled by steric as well as electronic effects. However, at low temperatures the Meerwein-Ponndorf-Verley reaction gains in Importance. This phenomenon is quantified by an isoinversion relationship.
