+ Site Statistics
+ Search Articles
+ PDF Full Text Service
How our service works
Request PDF Full Text
+ Follow Us
Follow on Facebook
Follow on Twitter
Follow on LinkedIn
+ Subscribe to Site Feeds
Most Shared
PDF Full Text
+ Translate
+ Recently Requested

Asymmetric synthesis using chiral acetals highly diastereoselective addition of organocerium reagents to chiral alpha aldoxime ether acetal



Asymmetric synthesis using chiral acetals highly diastereoselective addition of organocerium reagents to chiral alpha aldoxime ether acetal



Chemical and Pharmaceutical Bulletin 37(3): 602-605



Nucleophilic addition of organometallic reagents [organocerium reagents (RMgX-CeCl3, RLi-CeCl3), Grignard reagent, and organolithium reagents] to the chiral.alpha.-aldoxime-ether acetal (1) was studied. Among the reagents, organocerium reagents showed higher reactivity and stereoselectivity, giving the N-oxygenated chiral amine derivatives (6Aa-c) in a highly diastereoselective manner, whereas Grignard and organolithium reagents afforded no. 6. As an application of the reaction, the synthesis of (-)-N-acetylamphetamine (11) was achieved.

Please choose payment method:






(PDF emailed within 0-6 h: $19.90)

Accession: 007041338

Download citation: RISBibTeXText

DOI: 10.1248/cpb.37.602


Related references

Asymmetric synthesis of amino acids via catalytic reduction of azalactone-substituted acylaminoacrylic acids. 21. Catalytic asymmetric synthesis of the phenylethylamide of N-acyl-p-difluoromethoxyphenylalanine. Russian Chemical Bulletin 38(2): 351-354, 1989

Asymmetric synthesis using chiral acetals: Highly diastereoselective addition of organocerium reagents to chiral .ALPHA.-aldoxime-ether acetal. Chemical and Pharmaceutical Bulletin 37(3): 602-605, 1989

Asymmetric synthesis using chiral acetals highly diastereoselective addition of organocerium reagents to chiral alpha aldoxime ether acetal. Chemical and Pharmaceutical Bulletin 37(3): 602-605, 1989

Excellent chiral introduction by diene iron-tricarbonyl moiety. II: A formal synthesis of (+)- and (-)-frontalin using a diastereoselective 1,2-nucleophilic addition of organometallics into a (Z)-dienone Fe(CO)-3 complex. Chemical and Pharmaceutical Bulletin 44(5): 940-947, 1996

Asymmetric synthesis of α-methylaminoacids by the alkylation of glycine, alanine, and phenylalanine in chiral Ni(II) complexes. Russian Chemical Bulletin 36(12): 2595-2601, 1987

Asymmetric synthesis using chiral acetals: Highly diastereoselective nucleophilic addition of Grignard reagents to chiral 1-oxo-.BETA.-tetralone 1-acetals. Chemical and Pharmaceutical Bulletin 37(6): 1488-1492, 1989

Asymmetric synthesis using chiral acetals highly diastereoselective nucleophilic addition of grignard reagents to chiral 1 oxo beta tetralone 1 acetals. Chemical and Pharmaceutical Bulletin 37(6): 1488-1492, 1989

Asymmetric synthesis using chiral acetals. Studies on the nucleophilic addition of organometallics to chiral .ALPHA.-keto acetals in open-chain systems. Chemical and Pharmaceutical Bulletin 35(12): 4736-4746, 1987

Highly diastereoselective bis hydroxylation of a protected conduritol b a short route to myo inositol derivatives. Tetrahedron Letters 32(49): 7309-7312, 1991

Highlights of the Clean Air Act Amendments off 1990. Journal of the Air and Waste Management Association 41(1): 16-19, 1991

Asymmetric synthesis of cetirizine dihydrochloride. Tetrahedron Letters 43(6): 923-926, 4 February, 2002

Asymmetric synthesis of cyclic hydroxy ketones derived from enol ethers via sharpless asymmetric dihydroxylation A study in the correlation of the enol ether chain length and enantioselectivity. Journal Of Organic Chemistry. 68(21): 8088-8091, Ober 17, 2003

Asymmetric desymmetrization of meso-tetrahydrofuran derivatives by highly enantiotopic selective C-H oxidation. Tetrahedron. 54(35): 10339-10348,. 27, 1998

2-Methyl-5,6-dimethylenepyrimidin-4-one: A Novel Diene. Synlett 1993(5): 347-348, 1993

Asymmetric congenital deformity of the ribs. Collapse of the right side of the chest. Annals of Surgery 191(5): 534-538, 1980