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

Andrey P. Mityuk; Aleksandr V. Denisenko; Oleksandr P. Dacenko; Oleksandr O. Grygorenko; Pavel K. Mykhailiuk; Dmitriy M. Volochnyuk; Oleg V. Shishkin; Andrey A. Tolmachev

doi:10.1055/s-0029-1217137

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Synthesis 2010(3): 493-497
DOI: 10.1055/s-0029-1217137

PAPER

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

Andrey P. Mityuk^a, Aleksandr V. Denisenko^a, Oleksandr P. Dacenko^a, Oleksandr O. Grygorenko*^a,b, Pavel K. Mykhailiuk^a,b, Dmitriy M. Volochnyuk^a,c, Oleg V. Shishkin^d, Andrey A. Tolmachev^a,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)

Abstract
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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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