- A waste-minimized protocol for the preparation of 1,2-azido alcohols and 1,2-amino alcohols
-
Under solvent-free conditions the reaction of epoxides 1a-i with trimethylsilylazide (2) catalyzed by polystiryl-supported fluoride (PS-DABCOF2) has led to the efficient preparation of the corresponding O-TMS protected 1,2-azido alcohols 3a-i that, by treatment with Dowex-H, gave the related 1,2-azido alcohols 4a-i in excellent yields (83-99% and 82-96%, respectively). The use of a flow procedure has allowed us to significantly minimize waste in the preparation of representative 1,2-azido alcohols 4a, 4c and 4i that have been obtained with E-factors of 1.6, 2.1, and 1.9, respectively. The 1,2-amino alcohols 5a, 5c and 5f have been also prepared, in quantitative yields, by reduction of the corresponding O-TMS protected 1,2-azido alcohols 3a, 3c, and 3f by Pd on the Al2O3/HCOOH system.
- Ballerini, Eleonora,Crotti, Paolo,Frau, Ileana,Lanari, Daniela,Pizzo, Ferdinando,Vaccaro, Luigi
-
p. 2394 - 2400
(2013/09/12)
-
- Regio-selective synthesis of 1,2-aminoalcohols from epoxides and chlorohydrins
-
A simple and efficient procedure for the regio-selective synthesis of 1,2-aminoalcohols from terminal epoxides and chlorohydrins by using NaHMDS as the source of amine is reported. The wider scope and utility of this method is demonstrated.
- Murugan, Andiappan,Kadambar, Vasantha Krishna,Bachu, Sreekanth,Rajashekher Reddy,Torlikonda, Venkatarao,Manjunatha, Sulur G.,Ramasubramanian, Sridharan,Nambiar, Sudhir,Howell, Gareth P.,Withnall, Jane
-
supporting information
p. 5739 - 5741
(2012/11/06)
-
- Non-enzymatic kinetic resolution of β-amino alcohols using C-12 higher carbon sugar as a chiral auxiliary
-
An efficient non-enzymatic kinetic resolution strategy capable of accessing optically active β-adrenergic antagonists intermediates is reported. The C-12 higher carbon sugar derived from naturally occurring sucrose was employed to probe the kinetic resolution. Excellent enantiomeric excesses (ee >99%) and high yields were obtained under very mild conditions. The chiral auxiliary could be recovered in a high reclaimed ratio (>95%) and reusable form without any decrease of the resolving ability.
- Zhang, Jing-Yu,Liu, Hong-Min,Xu, Hai-Wei,Shan, Li-Hong
-
p. 512 - 517
(2008/09/19)
-
- CARBOXAMIDE DERIVATIVE
-
An SGLT inhibitor comprising a compound of the formula: (|) wherein the ring A is an optionally substituted ring; R1 is an optionally substituted hydrocarbon group, etc.; each of R2 and R3 independently is a hydrogen atom, an optionally substituted hydrocarbon group, etc.; R4 is an optionally substituted hydrocarbon group, etc.; and X is a bivalent chain group whose main chain consists of 1 to 6 atoms. This SGLT inhibitor is useful as a preventive/therapeutic agent for diabetes mellitus, obesity, hypertension, hyperlipemia, etc.
- -
-
Page/Page column 67-68
(2010/11/08)
-
- A General Route to the Synthesis of N-Protected 1-Substituted and 1,2-Disubstituted Taurines
-
N-Benzyloxycarbonyl protected α-substituted and αβ- disubstituted taurines were synthesized from olefins and epoxides via N-benzyloxycarbonylamino alcohol thioacetates as key intermediates. They are important sulfur analogues of naturally occurring amino acids and building blocks for the synthesis of α-substituted and α,β- disubstituted β-sulfonopeptides.
- Xu, Jiaxi,Xu, Shu
-
p. 276 - 282
(2007/10/03)
-
- Regioselective opening of epoxides to β-amido alcohols under solid-liquid PTC conditions
-
A study on the ring opening of a number of epoxides 1 with trifluoroacetamide (2) under solid-liquid phase transfer catalysis (SL-PTC) conditions has been performed. The reaction is completely regioselective affording β-amido alcohols 3 deriving from the attack of the nucleophile to the less substituted carbon atom of the oxirane ring.
- Albanese, Domenico,Landini, Dario,Penso, Michele
-
p. 4787 - 4790
(2007/10/03)
-
- Thiazolidine and oxazolidine derivatives, their preparation and their medical use
-
Compounds of formula (I): STR1 and salts, esters and solyates thereof and pro-drugs therefor are useful for the treatment and/or prophylaxis of a variety of disorders, including one or more of: hyperlipemia, hyperglycemia, obesity, glucose tolerance insufficiency, insulin resistance and diabetic complications.
- -
-
-
- Synthesis and psychotrope evaluation of new 3-ureidopropan-2-ols using the skin conductance reaction (SCR)-habituation test
-
The syntheses of 1-substituted 3-ureidopropan-2-ols 2 and 3-acetyl-5-(phenyl-4-piperazinyl)methyl-2-oxazolidinones 5 from the corresponding 2-amino-2 oxazolines 1 are described. Some of these compounds have been investigated for psychotropic activity in m
- Forfar,Jarry,Quermonne,Boulouard
-
p. 761 - 766
(2007/10/02)
-
- TiCl4 Induced Opening of Chiral Acetals: a route to β-adrenergic blocking agents
-
Aryloxy and alkyloxypropanolamines 7a-c are obtained in 45 to 70 percent yields and with asymmetric induction, using TiCl4 induced nucleophilic addition of cyanotrimethylsilane onto chiral acetals derived from racemic 2,4-pentanediol.Therefore, optically pure 2,4-pentanediol will provide, after a purification, optically pure 7a-c.
- Solladie-Cavallo, A.,Suffert, J.,Gordon, M.
-
p. 2955 - 2958
(2007/10/02)
-