Synthesis Of Β-amino Alcohols Research Articles

Synthesis of β-amino alcohols by regioselective ring opening of arylepoxides with anilines catalyzed by cobaltous chloride

CoCl 2 has been used as a mild and effective catalyst for regioselective ring opening of oxiranes with anilines to synthesize β-amino alcohols in good yields.

Asymmetric synthesis of β-amino alcohol by reductive cross-coupling of planar chiral ferrocenecarboxaldehyde with N-tosyl ferrocenylideneamine, and its application to asymmetric reaction

Samarium iodine-mediated cross-coupling of N-tosyl ferrocenylideneamine with planar chiral ferrocenecarboxaldehyde gave diastereoselectively anti-β-amino alcohol derivative in good yield. The obtained anti-β-amino alcohol with ferrocene ring at 1,2-positions was utilized as chiral auxiliary for asymmetric alkylation and acylation reactions.

Enolboration of Conjugated Ketones and Synthesis of β‐Amino Alcohols and Boronated α‐Amino Acids

AbstractFor Abstract see ChemInform Abstract in Full Text.

Utilization of industrial waste materials. Part 14.† Synthesis of β-amino alcohols and thiols with a 2-azabicyclo[3.3.0]octane backbone and their application in enantioselective catalysis

New, chiral β-tert-amino tert-alcohols have been synthesized from the enantiomerically pure sec-amine (all-R)-1b via the new glycine, alanine and phenylglycine derivatives 2–6. Grignard additions to these esters provided the new rigid amino alcohols 7–11 in fair yields. The absolute configurations of the stereogenic centers, which arose during the alkylation step, were assigned by an independent route leading to some of the optical antipodes of 7–10. Condensation of enantiomerically pure β-amino alcohols 13a–g, 16 and 17 with γ-ketoester rac-12 afforded the N,O-acetals 14a–g, 18 and 19, which were subsequently reduced to the β-tert-amino alcohols 10a,c and 15a–g. X-Ray analysis of compound 19 was performed to verify the stereochemistry observed by chemical correlation. The nucleophilic ring opening of enantiomerically pure styrene oxide by amine 1b resulted in the formation of regioisomeric amino alcohols 9a, 21a, and 10a, 21b. Amino thiol derivatives 22 and 25a,b were prepared by treatment of 10a and 15a,b, respectively, with methanesulfonyl chloride followed by regio- and stereoselective cleavage of the in situ formed aziridinium ions with potassium thioacetate. Reduction of these compounds to thiols 23 and 26a,b and subsequent oxidation afforded amino disulfides 24 and 27a,b. Finally, the bicyclic β-amino alcohols and thiols were used as chiral ligands in the enantioselective addition of diethylzinc to benzaldehyde and ee values up to 96% were found.

Stereocontrolled approaches to (+)- and (−)-γ-trifluoromethyl-GABOB, a new hydroxymethylene (statine) dipeptide isostere

Two efficient approaches to both enantiomers of syn-γ-trifluoromethyl γ-amino β-hydroxy butyric acid (γ-Tfm-GABOB) ( 10), a new hydroxymethylene (statine) dipeptide isostere, are described. One exploits the recently disclosed `non-oxidative' Pummerer reaction, by means of which α-lithium alkyl sulfoxides are used as chiral α-hydroxyalkyl anion equivalents in the synthesis of β-amino alcohols. Trifluoropyruvaldehyde- N, S-ketal ( R)- 11, a novel stereochemically stable synthetic equivalent of α-amino trifluoropropanal, is used in the second approach.

Diastereoselective Synthesis of beta-Amino Alcohols via Bu(3)SnH-Mediated Reductive Cyclization of Carbonyl-Oxime Ethers.

Diastereoselective Synthesis of beta-Amino Alcohols via Bu(3)SnH-Mediated Reductive Cyclization of Carbonyl-Oxime Ethers.

Diastereoselective synthesis of β-amino alcohols with two or three chiral centers.

Diastereoselective synthesis of β-amino alcohols with two or three chiral centers.

A new synthesis of β-amino alcohols

A new synthesis of β-amino alcohols