Highly diastereoselective coupling reactions between chiral benzaldehyde tricarbonylchromium complexes and activated double bonds

Article Article scientifique Article Highly diastereoselective coupling reactions between chiral benzaldehyde tricarbonylchromium complexes and activated double bonds eng 1993 author Kundig Ernst Peter 26401 author Xu Longhe 22345 author Romanens Patrick 22629 author Bernardinelli Gérald Hugues 24765 7049-7052 10.1016/S0040-4039(00)61594-0 0040-4039 The amine catalyzed coupling reaction of acrylic derivatives with benzaldehydes (Baylis-Hillman reaction) is more efficient when the arene is complexed to the electrophilic Cr(CO)3 group. Reactions with planar chiral o-substituted benzaldehyde complexes are highly diastereoselective. 3-Hydroxy-2-methylenealkanoic acid derivatives can be obtained efficiently and with very high enantiomeric excess from readily accessible enantiomerically pure complexes. The configuration of the benzylic stereogenic center relative to the planar chirality of the arene complex was determined in one case by an X-ray structural analysis. The reaction has been extended to an o-anisaldehydeimine complex. Dewey 540 36 Département de chimie organique 141 false Tetrahedron letters 34 44 bd1d0732-ec9f-41a7-9a43-ece303b47baa Article (Published version) Restricted Kundig_TL_1993347049.pdf 2688466 application/pdf Vignette Public bonds.gif 4996 image/gif restrictedAccess Faculté des sciences / Section de chimie et biochimie / Département de chimie organique

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Highly diastereoselective coupling reactions between chiral benzaldehyde tricarbonylchromium complexes and activated double bonds	Tetrahedron letters			1993	701	0

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