Decarboxylative Aldol-Type Reaction
of 2-(Trifluoroacetyl)-1,3-diazoles with Activated Acetic Acids

Pavel V. Khodakovskiy; Dmitriy M. Volochnyuk; Andrey A. Tolmachev

doi:10.1055/s-0028-1087985

PAPER

Decarboxylative Aldol-Type Reaction of 2-(Trifluoroacetyl)-1,3-diazoles with Activated Acetic Acids

Pavel V. Khodakovskiy^a,b, Dmitriy M. Volochnyuk*^a,c, Andrey A. Tolmachev^b
^a Enamine Ltd., 23 Alexandra Matrosova st., 01103 Kyiv, Ukraine
Fax: +380(44)5373253; e-Mail: D.Volochnyuk@enamine.net;
^b National Taras Shevchenko University, 62 Volodymyrska st., 01033 Kyiv-33, Ukraine
^c Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Murmanska 5, 02094 Kyiv-94, Ukraine

Abstract

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Abstract

The highly electrophilic ketones 2-(trifluoroacetyl)-1,3-diazoles easily undergo a decarboxylative aldol-type reaction with activated acetic acids to afford heterocyclic trifluoromethyl-substituted alcohols bearing various functionalities.

Key words

heterocycles - 1,3-diazoles - aldol reactions - trifluoromethyl compounds - alcohols

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References

1a Singh RP. Shreeve JM. Tetrahedron 2000, 56: 7613

1b Prakash GKS. Yudin AK. Chem. Rev. 1997, 97: 757

1c Umemoto T. Chem. Rev. 1996, 96: 1757

1d Burton DJ. Yang Z.-Y. Tetrahedron 1992, 48: 189

1e McClinton MA. McClinton DA. Tetrahedron 1992, 48: 6555

2a Lin P. Jiang J. Tetrahedron 2000, 56: 3635

2b Nenaidenko VG. Sanin AV. Balenkova ES. Russ. Chem. Rev. 1999, 437

2c Bégué J.-P. Bonnet-Delpon D. Tetrahedron 1991, 47: 3207

3 Khodakovskiy PV. Volochnyuk DM. Panov DM. Pervak II. Zarudnitskii EV. Shishkin OV. Yurchenko AA. Shivanyuk A. Tolmachev AA. Synthesis 2008, 948

4 McBee ET. Kim YS. Braendlin HP. J. Am. Chem. Soc. 1962, 84: 3154

5a Chkanikov ND. Shidlovskii AF. Mukhanov VI. Golubev AS. Peregudov AS. Mendeleev Commun. 2006, 3: 175

5b Saloutin VI. Piterskikh IA. Pashkevich KI. Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.) 1982, 31: 1687