Sergey Sergeyev

 

Postdoctoral Fellow

Location:

HCI G-312

Phone:

+41-1-632 2998

e-mail:

Sergey Sergeyev

Education

1988-1993:

Study of chemistry at Lomonosov University in Moscow

1993-1999:

Research fellow at the Russian Academy of Science in Moscow

1999-2002:

Ph.D. with Prof.M. Hesse at the University Zürich

2002-present:

Postdoc with Prof. F. Diederich at ETH Zurich

Project

Two enantiomeric trans-2 bisadducts of C60 prepared from Tröger’s base bismalonate derivative

Bisadducts of C60 with trans-1, trans-2, trans-3 and trans-4 addition pattern were regio- and diastereoselelectively synthesized in high yield using bismalonates tethered by the structural core of Tröger’s base. Moreover, both enantiomers of the trans-2 adduct with inherently chiral addition pattern were prepared from non-racemic tethers. This represents the first example for an application of Tröger's base as chiral auxiliary in asymmetric synthesis.

Publications

Papers

S. Sergeyev, F. Diederich, Angew. Chem. 2004, 116, 1770, Angew. Chem. Int. Ed. 2004, 43, 1738. Bringing Two Fascinating Molecules Together: Derivatives of Tröger’s Base in the Regio- and Stereoselective Tether-Directed Remote Functionalization of C60.

C. Thilgen, S. Sergeyev, F. Diederich, , Top. Curr. Chem. 2004, in press. Tether-Directed Remote Functionalization of Fullerenes (review).

S. Sergeyev, M. Schär, P. Seiler, F. Diederich, in preparation. Derivatives of Tröger’s Base in the Regio- and Stereoselective Tether-Directed Remote Functionalization of C60.

B. Frydman, S. Bhattacharya, A. Sarkar, K. Drandarov, S. Chesnov, A. Guggisberg, K. Popaj, S. Sergeyev, A. Yurdakul, M. Hesse, H. S. Basu, L. J. Marton, J. Med. Chem. 2004, 47, 1051. Macrocyclic Polyamines Deplete Cellular ATP Levels and Inhibit Cell Growth in Human Prostate Cancer Cells.

S. A. Sergeyev, M. Hesse, Helv. Chim. Acta 2003, 86, 465. Alkaloid (–)-(S)-Neoperiphylline: Revision of the Structure Based on the Total Synthesis.

S. A. Sergeyev, M. Hesse, Helv. Chim. Acta 2003, 86, 750. Enamides via Long-distance Migration of Double Bonds.

S. A. Sergeyev, M. Hesse, Synlett 2002, 1313. A New Convenient Method for the Preparation of Enamides from N-Allylamides.

S. A. Sergeyev, M. Hesse, Helv. Chim. Acta 2002, 85, 161. A Novel Synthesis of the Macrocyclic Spermidine Alkaloid (+)-(S)-Dihydroperiphylline.

O. A. Fedorova, S. P. Gromov, Yu. V. Pershina, S. A. Sergeyev, Yu. P. Strokach, V. A. Barachevsky, M. V. Alfimov, G. Pèpe, A. Samat, R. Guglielmetti, J. Chem. Soc., Perkin Trans. 2 2000, 563. Novel Azacrown Ether-containing Spiro(indoline-2,3'-naphtho¬oxazines): Design, Synthesis, and Cation Dependent Photochromism.

S. P. Gromov, S. A. Sergeyev, S. I. Druzhinin, M. V. Rusalov, B. M. Uzhinov, L. G. Kuzmina, A. V. Churakov, J. A. K. Howard, M. V. Alfimov, . Chem. Bull. 1999, 48, 525. Crown Ether Butadienyl Dyes. Synthesis, Structure, Fluorescence and Complexation of Chromogenic Aza-15-crown-5 Ether.

O. A. Fedorova, S. P. Gromov, Yu. P. Strokach, Yu. V. Pershina, S. A. Sergeyev, V. A. Barachevsky, G. Pepe, A. Samat, R. Guglielmetti, M. V. Alfimov, Russ. Chem. Bull. 1999, 48, 1950. Crown-containing spirooxazines and spiropyrans. 1. Synthesis and Anion-"Capped" Complexes of Photochromic Aza-15-crown-5 Ethers with Flexible Spacers.

S. I. Druzhinin, M. V. Rusalov, B. M. Uzhinov, S. P. Gromov, S. A. Sergeyev, M. V. Alfimov, , J. Fluorescence 1999, 9, 33. Fluorescence of Crowned Butadienyl Dye and Its Metal Complexes.

S. P. Gromov, M. A. Razinkin, V. S. Drach, S. A. Sergeyev, Russ. Chem. Bull. 1998, 47, 1179. Reaction of Quinazolinium Salts with Heterocyclic Quaternary Salts Yielding 3-Hetaryl¬quinolines.

S. Zolotareva, S. N. Nikolaeva, E. V. Klimkina, S. A. Sergeyev, S. V. Ponomarev, V. S. Petrosyan, J. General Chemistry (Zhurnal Obshchei Khimii, in Russian). 1996, 66, 1150. Organogermanium Derivatives of Mandelic and Lactic Acids.

Patents

S. P. Gromov, S. A. Sergeyev, O. A. Fedorova, Yu. P. Strokach, S. N. Dmitrieva, V. A. Barachevsky, M. V. Alfimov, Eur. Pat. Appl. 2000, EP 1044879. 1-[(N-(Un)¬sub¬stituted amido¬alkyl]¬spiro¬indolinonaphthoxazines, Their Preparation, Compositions, and Polymer Matrices Containing Them.

S. P. Gromov, N. A. Kurchavov, S. A. Sergeyev, Russ. Pat. 2000, RU 2150466. Method of Synthesis of 4-Arylpyridines.

Book

S. A. Sergeyev. Getting prepared to the High School Exam in Chemistry (in Russian), ISBN 5-85684-229-4. Aquarium Publ., Moscow, 1997 (2nd edition 2000).