54680-46-5Relevant articles and documents
Chiral-Organotin-Catalyzed Kinetic Resolution of Vicinal Amino Alcohols
Yang, Hui,Zheng, Wen-Hua
, p. 16177 - 16180 (2019/11/03)
A highly efficient kinetic resolution of racemic amino alcohols has been achieved for the first time with a chiral tin catalyst. A chiral organotin compound with 3,4,5-trifluorophenyl groups at the 3,3′-positions of the binaphthyl framework enabled this transformation with excellent yield and high enantioselectivity. The process tolerates aryl- and alkyl-substituted amino alcohols and a variety of other substrates, affording the corresponding products in high enantioselectivity and with s factors up to >500.
Regio- and stereoselective multi-enzymatic aminohydroxylation of β-methylstyrene using dioxygen, ammonia and formate
Corrado, Maria L.,Knaus, Tanja,Mutti, Francesco G.
, p. 6246 - 6251 (2019/12/03)
We report an enzymatic route for the formal regio- and stereoselective aminohydroxylation of β-methylstyrene that consumes only dioxygen, ammonia and formate; carbonate is the by-product. The biocascade entails highly selective epoxidation, hydrolysis and hydrogen-borrowing alcohol amination. Thus, β-methylstyrene was converted into 1R,2R and 1S,2R-phenylpropanolamine in 59-63% isolated yields, and up to >99.5 : 0.5 dr and er.
Direct catalytic synthesis of unprotected 2-amino-1-phenylethanols from alkenes by using iron(II) phthalocyanine
Legnani, Luca,Morandi, Bill
supporting information, p. 2248 - 2251 (2016/02/18)
Aryl-substituted amino alcohols are privileged scaffolds in medicinal chemistry and natural products. Herein, we report that an exceptionally simple and inexpensive FeII complex efficiently catalyzes the direct transformation of simple alkenes into unprotected amino alcohols in good yield and perfect regioselectivity. This new catalytic method was applied in the expedient synthesis of bioactive molecules and could be extended to aminoetherification.
Charge-transfer interactions: An efficient tool for recycling bis(oxazoline)-copper complexes in asymmetric henry reactions
Didier, Dorian,Magnier-Bouvier, Caroline,Schulz, Emmanuelle
supporting information; experimental part, p. 1087 - 1095 (2011/07/09)
An anthracenyl-modified chiral bis(oxazoline) copper complex has been demonstrated to efficiently promote nitroaldol reactions between structurally varying aldehydes and nitromethane or nitroethane. The catalyst was recovered through formation of a charge transfer complex between the chiral ligand and trinitrofluorenone and its subsequent precipitation with pentane. The efficiency of this procedure was proved through several consecutive catalytic cycles that allowed the sturdy formation of the expected product with a high enantioselectivity. The catalyst′s stability was also put to the test in an original multi-substrate procedure. Following the same recovery concept, a new heterogeneous procedure was tested for which trinitrofluorenone was covalently linked to a silica support. Asymmetric heterogeneous catalysis was performed under these conditions as one of the few examples demonstrating the potential catalyst recycling in nitroaldol reactions through reversible, non-covalent interactions. Copyright
Synthesis of 1,2-diamino-1-phenylpropane diastereoisomers from u-N-trifluoroacetyl-2-amino-1-phenylpropan-1-ol
Dufrasne, Francois,Neve, Jean
, p. 739 - 746 (2007/10/03)
A new simple procedure for the synthesis of diastereomeric 1,2-diamino-1-phenylpropanes starting from u-N-trifluoroacetyl-2-amino-1- phenylpropan-1-ol (N-trifluoroacetylnorephedrine) is described. The trifluoroacetyl protecting group was particularly suit
β-Amino alcohols from amino acids: Chelation control via Schiff bases
Polt,Peterson
, p. 4985 - 4986 (2007/10/02)
Sequential addition of iBu2AlH and RLi or RMgX to Schiff base esters derived from amino acids provides a simple route to β-amino alcohols. The reaction procedes without racemization, and with high threo selectivity. Several representative sphingosines are synthesized.
Stereoselectrive Syntheses of Ephedrine and Related 2-Aminoalcohols of High Optical Purity from Protected Cyanohydrins
Jackson, W. Roy,Jacobs, Howard A.,Matthews, Barry R.,Jayatilake, Gamini S.,Watson, Keith G.
, p. 1447 - 1450 (2007/10/02)
Ephedrine and related optically active β-aminoalcohols can be prepared by zinc borohydride reduction of aryl O-protected magnesium imines and aryl α-hydroxyimimes which in turn are readily available from optically active cyanohydrins.
