An Unprecedented Stereoselective Titanium-Mediated Dihydrodimerization of Allyl Ethers and Allylamines

Armin de Meijere; Björn Stecker; Alexandre Kourdioukov; Craig M. Williams

doi:10.1055/s-2000-6297

Synthesis 2000; 2000(7): 929-934
DOI: 10.1055/s-2000-6297

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An Unprecedented Stereoselective Titanium-Mediated Dihydrodimerization of Allyl Ethers and Allylamines

Armin de Meijere^* , Björn Stecker, Alexandre Kourdioukov, Craig M. Williams

^*Institut für Organische Chemie, Georg-August-Universität Göttingen, Tammannstrasse 2, D-37077 Göttingen, Germany; Fax +49(0)551399475; E-mail: ameijer1@uni-goettingen.de

Abstract

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3-Phenylallyl ether 17, 2,5-dihydrofuran (1) and N-acceptor-substituted 2,5-dihydropyrrols 4, 6, 8, 10, 12 upon treatment with cyclohexylmagnesium bromide in the presence of Ti(Oi-Pr)₄ were found to undergo a diastereoselective dihydrodimerization affording 1,5-dienes, d,l-2,3-diethenylbutane-1,4-diol (51% yield) and d,l-2,3-diethenyl-1,4-bis(sulfonylamino)butanes (43 - 52%), respectively. In the presence of titanium bis(4R,5R)-taddolate, the dihydrodimerization of 1 proceeded with 35 - 38% chemical yield and up to 94% ee.

titanacyclopropanes - metal-mediated C,C-bond formation - diastereoselectivity - 1,4-diols - 1,4-diamines

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