+ 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 nucleophilic addition of grignard reagents to chiral 1 oxo beta tetralone 1 acetals



Asymmetric synthesis using chiral acetals highly diastereoselective nucleophilic addition of grignard reagents to chiral 1 oxo beta tetralone 1 acetals



Chemical & Pharmaceutical Bulletin 37(6): 1488-1492



Nuccleophilic addition or organometallic reagents (Grignard reagents and organolithium reagents) to two chiral 1-oxo-.beta.-tetralone 1-acetals (1a,b) was studied. Extremely high stereoselectivity was achieved in the reactions of 1a and 1b with Grignard reagents leading to the .alpha.-hydroxy acetals (6) bearing a chiral tertiary alcohol moiety at the homobenzylic position. The stereochemistry of the products derived from 1a was determined by correlation with compound 9 and that of the products derived from 1b was determined by consideration of the circular dichroism spectrum of the benzoate (11) prepared from 6bC.

Please choose payment method:






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

Accession: 007041339

Download citation: RISBibTeXText

DOI: 10.1248/cpb.37.1488


Related references

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

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

Asymmetric synthesis using chiral acetals: Studies on the nucleophilic addition of organometallics to chiral x-keto acetals in cyclic systems. Chemical & Pharmaceutical Bulletin 35(6): 2305-2313, 1987

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

Asymmetric synthesis using chiral acetals: Highly stereoselective reduction of chiral .ALPHA.-keto-.BETA.,.GAMMA.-unsaturated acetals and its application for the synthese of (R)-(-)- and (S)-(+)-3'-methoxy-4'-O-methyljoubertiamine. Chemical & Pharmaceutical Bulletin 37(8): 2047-2052, 1989

Asymmetric synthesis using chiral acetals highly stereoselective reduction of chiral alpha keto beta gamma unsaturated acetals and its application for the syntheses of r levo and s dextro 3' methoxy 4' o methyljoubertiamine. Chemical and Pharmaceutical Bulletin 37(8): 2047-2052, 1989

Diastereoselective synthesis of axially chiral biaryls via nucleophilic addition to chromium complexes with Grignard reagents. Tetrahedron Letters 37(35): 6359-6362, 1996

Asymmetric syntheses using tert-leucine. 1. An asymmetric synthesis of beta-substituted aldehydes via 1,4-addition of Grignard reagents to chiral alpha, beta-unsaturated aldimines. Journal of the American Chemical Society 98(23): 7450-7459, 1976

Novel asymmetric desymmetrization of meso-1,2-diols via diastereoselective beta-elimination of chiral alpha-arylsulfinyl acetals. Tetrahedron 52(19): 6527-6546, 1996

Excellent chiral introduction by diene iron-tricarbonyl moiety. III: Asymmetric synthesis of hydroxyethylidene dipeptide isostere using a diastereoselective 1,2-nucleophilic addition of organocerium reagents into a 1-azatriene Fe(CO)-3 complex. Chemical and Pharmaceutical Bulletin 44(5): 948-955, 1996

Asymmetric addition of Grignard reagents to chiral 1-acylpyridinium salts; A chiral auxiliary study. Tetrahedron Letters 37(22): 3807-3810, 1996

Asymmetric synthesis of 1-aryl-1,2,3,4-tetrahydroisoquinolines Part 1 Addition of chiral phenylacetaldehyde acetals to acylimines. Tetrahedron Letters 36(44): 8003-8006, 1995

Asymmetric Addition Reactions of Grignard Reagents to Chiral Fluoral Hemiacetal: Asymmetric Synthesis of 1-Substituted-2,2,2-Trifluoroethylamines. Synlett 1997(12): 1381-1382, 1997

Diastereoselective conjugate addition with acetals oxazolidines and imidazolidines as chiral auxiliaries. Tetrahedron Letters 29(35): 4411-4414, 1988