Oxidation of allylselenides with the Sharpless AD-reagents

[en] Allylselenides are efficiently oxidized by AD-mix reagents. Oxidation takes chemoselectively place on the selenium atom of allylselenides bearing a methylseleno or a phenylseleno moiety, but chemoselectively occurs on the C,C double bond of the corresponding o-nitrophenyl derivatives.

Disciplines :

Chemistry

Author, co-author :

Krief, Alain; Facultés Universitaires Notre-Dame de la Paix - Namur - FUNDP > chimie

Colaux, Catherine ; Facultés Universitaires Notre-Dame de la Paix - Namur - FUNDP > Chimie > Chimie Organique

Dumont, willy; Facultés Universitaires Notre-Dame de la Paix - Namur - FUNDP > chimie

Language :

English

Title :

Oxidation of allylselenides with the Sharpless AD-reagents

Publication date :

1997

Journal title :

Tetrahedron Letters

ISSN :

0040-4039

Publisher :

Elsevier, Oxford, United Kingdom

Volume :

Issue :

Pages :

3315 - 3318

Peer reviewed :

Peer Reviewed verified by ORBi

Additional URL :

http://www.sciencedirect.com/science/article/B6THS-3S9RB4B-1X/2/afd8300876c65e26d61b4ceaa90cc493

Available on ORBi :

since 05 April 2012

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Bibliography

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(c) 2,3-dihydroxy-1-phenylthiohexane was obtained, as already reported, from AD-mix-β (71 % yield, 92 % e.e.) and in lower yield and e.e. from AD-mix-α (55 % yield, 77% e.e.).
The purity of the diols 5 was assessed by chiral HPLC on a 25 cm column : DAICEL CHIRACEL OD-H, cellulose carbamate phase supported on 5μm silica-gel, 1 ml/ min, UV detector 254 nm., Retention time (min., hexane : 2propanol= 97:3)= 5′a : 19.81, 5″a : 25.12; (min., hexane : 2-propanol= 90:10) 5c″ : 26.17, 5c′ : 28.46. Their absolute stereochemistry was derived from the Sharpless rules.5a,b
Clarembeau, M.; Krief, A. Tetrahedron Lett. 1984, 25, 3625.
Grieco, P. A.; Oilman, S.; Nishizawa, M. J. Org. Chem. 1976, 41,1485.
Krief, A.; Laval, A-M. Synlett, submitted.
The allyl phenyl selenides bearing a terminal C,C double bond are prone to isomerise to the corresponding terminal selenides.1j,2f We however found in this study that the allyl o-nitrophenyl selenide 7c does not rearrange under a large variety of conditions : UV (solar lamp, 2.5h; TsOH, benzene, 20°C, 6h or 80°C, 5h).