4_1_05 - , -unsaturated carbonyl compound or related...

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Massachusetts Institute of Technology Organic Chemistry 5.512 April 1, 2005 Prof. Rick L. Danheiser Unit 3 Stereocontrolled Conjugate Addition inisi i i Mi l i l i i l l l i i i i l ili i l i i j iti Unsta ze ucleo es l i i j iti Conjugat educ on l i i j iti a e chae ons) Intr c Stereochem stry n the chae React on Substrate Contro : Asymmetr c Induct on by Mo ecu ar Framework Substrate Contro : Asymmetr c Induct on v a Ch ra Aux ar es Cata yt c Asymmetr c Con ugate Add on I: bili d N phil Cata yt c Asymmetr c Con ugate Add on II: e R ti Cata yt c Asymmetr c Con ugate Add on III: St bili phil s (Mi l Additi Definitions Conjugate Addition Addition of a nucleophile to an alkene or alkyne conjugated with an electron-withdrawing group Michael Reaction Addition of an enolate or related "stabilized" carbanionic species to an
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Unformatted text preview: , -unsaturated carbonyl compound or related electron-deficient alkene or alkyne General References Conjugate Addition Reactions in Organic Synthesis", P. Perlmutter, Pergamon Press, 1992 Reviews: "Enantioselective Conjugate Additions"; M. P. Sibi; S. Manyem Tetrahedron 2000, 56, 8033. "Recent Advances in Catalytic Enantioselective Michael Additions"; N. Krause; A. Hoffmann-Rder Synthesis 2001, 171 Review Reading Assignment Carey and Sundberg "Advanced Organic Chemistry" Part B Section 1.10 (Alkylation of Carbon Nucleophiles by Conjugate Addition) Section 7.3.1 (Organozinc Compounds) Section 8.1 (Organocopper Intermediates) Section 9.1.1 (Synthesis of Organoboranes)...
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