Catalytic asymmetric dihydroxylation of alpha-methylstyrene by air

[en] Dioxygen is able, under visible irradiation, to promote the high yielding and highly asymmetric dihydroxylation of alpha-methylstyrene in the presence of catalytic amounts of Os(VI), phthalazine dihydroquinidine chiral ligand [(DHQD)(2)PHAL]. (C) 1999 Published by Elsevier Science Ltd. Ail rights reserved.

Disciplines :

Chemistry

Author, co-author :

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

Colaux, Catherine ; Université de Liège - ULiège > Gembloux Agro-Bio Tech > Gembloux Agro-Bio Tech

Language :

English

Title :

Catalytic asymmetric dihydroxylation of alpha-methylstyrene by air

Publication date :

1999

Journal title :

Tetrahedron Letters

ISSN :

0040-4039

Publisher :

Elsevier, Oxford, United Kingdom

Volume :

Issue :

Pages :

4189-4192

Peer reviewed :

Peer Reviewed verified by ORBi

Available on ORBi :

since 08 October 2009

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Bibliography

a) Kolb, H, C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483;
b) These reactions can be performed using commercially available premixes which are available from Aldrich Chemical Co [AD-mix-α n° 39,275-8; AD-mix-β n° 39,276-6].
a) Corey, E. J.; Noe, M. C. J. Am. Chem. Soc. 1996, 118, 319;
b) DelMonte, A. J.; Haller, J.; B) Sharpless, K. B.; Singleton, D. A.; Strassner, T.; Thomas, A. A. J. Am. Chem. Soc. 1997, 119, 9907;
c) Rouhi, A. M. C&EN 1997, November Issue, p23.
a) E.N. Jacobsen, I. Marko, W. S. Mungall, G. Schroder, K. B. Sharpless J. Am. Chem. Soc. 1988, 110, 1968;
b) J. S. M. Wai, I. Marko, J. S. Svendsen, M. G. Finn, E. N. Jacobsen and K. B. Sharpless J. Am. Chem. Soc. 1989, 111, 1123 ;
c) In the original work, 3a the AD reaction has not been carried out on α-methylstyrene and NMO with the "bystander" methoxyquinoleine.1 We have checked that the reaction provides, using (DHQD)2PHAL as the ligand and under normal conditions (no slow addition of NMO)1,3b results similar to those described in the original paper (ee 67%).3a
a) Torii, S.; Liu, P.; Bhuvaneswari, N.; Amatore, C.; Jutand, A. J. Org. Chem. 1996, 61, 3055 and references cited;
b) Torii, S.; Liu, P.; Tanaka, H. Chem. Lett. 1995, 319.
a) for "Singlet Oxygen mediated Asymmetric Diydroxylation";
b) for "SelenOxide mediated Asymmetric Diydroxylation".
L. Hevesi, A. Krief Angew. Chem. Int. Ed. Engl. 1976, 15, 381.
A.G. Abatjoglou, D. R. Bryant Tetrahedron Lett. 1981, 22, 2051.
a) H. Becker, K. B. Sharpless Angew. Chem. Int. Ed. Engl. Ed. 1996, 35, 448;
b) [α]25 D= -5.28 ( c = 0.97, EtOH )8a or [α]24D = -4.89 (c = 3.9, EtOH).
These results will be described later.
F. Jensen, A. Greer, E. L. Clennan J. Am. Chem. Soc. 1998, 120, 4439.
The following amount of reagents (in mg) has been used to oxidize 1 mmol of α-methylstyrene in aqueous t- BuOH by the original Sharpless AD reaction using Admix or our SOAD reaction. (AD/SOAD): K2OsO2(OH)4 (1.45/ 4.6); (DHQD)2PHAL (7.7/17.9); K2CO3(411/41); K3Fe(CN)6 (979/-); PhSeCH2Ph (-/20) rose bengale (-/3); overall (1400/87).