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Synthesis 2010(3): 493-497  
DOI: 10.1055/s-0029-1217137
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

An Approach to Azabicyclo[n.3.1]alkanes by Double Mannich Reaction

Andrey P. Mityuka, Aleksandr V. Denisenkoa, Oleksandr P. Dacenkoa, Oleksandr O. Grygorenko*a,b, Pavel K. Mykhailiuka,b, Dmitriy M. Volochnyuka,c, Oleg V. Shishkind, Andrey A. Tolmacheva,b
a Enamine Ltd., Alexandra Matrosova Street 23, Kyiv 01103, Ukraine
b Department of Chemistry, Kyiv National Taras Shevchenko University, Volodymyrska Street 64, Kyiv 01033, Ukraine
Fax: +380(44)5024832; e-Mail: gregor@univ.kiev.ua;
c Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Murmanska Street 5, Kyiv 02660, Ukraine
d STC ‘Institute for Single Crystals’, National Academy of Science of Ukraine, 60 Lenina ave., Kharkiv 61001, Ukraine
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Publication History

Received 29 September 2009
Publication Date:
20 November 2009 (online)

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Abstract

Chlorotrimethylsilane-promoted double Mannich annulation of ketones using N,N-bis(methoxymethyl)benzylamine has been explored. It has been shown that the structure of the substrate drastically influenced the outcome of the reaction. The method allows azabicyclo[n.3.1]alkane derivatives (n = 2-5) to be obtained in good yields.

Key words

annulation - Mannich bases - molecular rigidity - bicyclic compounds - chlorotrimethylsilane

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