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Synfacts 2009(9): 1040-1040  
DOI: 10.1055/s-0029-1217793
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

Lewis Base Catalysts Containing Axial Chirality of Allenes

Contributor(s): Benjamin List, Saihu Liao
X. Pu, X. Qi, J. M. Ready*
The University of Texas Southwestern Medical Center at Dallas, USA
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Publikationsverlauf

Publikationsdatum:
21. August 2009 (online)

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Significance

A series of optically active allene-containing phosphine oxides (like 3-5) were synthesized and investigated as Lewis base catalyst in the ring opening of meso-epoxides. In the presence of 0.1 to 2 mol% of catalyst 3, a set of meso-epoxides 1 can be efficiently opened by SiCl4 with high enantioselectivity providing the corresponding enantioenriched chlorohydrins 2 with up to 97:3 er, while ortho-substituted stilbenes showed no reactivity and aliphatic epoxides (linear or cyclic) proceeded with lower stereoselectivity.