4_4_05 - T Hayashi et al Chem Rev 2003 103 2829 and Bull...

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Massachusetts Institute of Technology Organic Chemistry 5.512 April 4, 2005 Prof. Rick L. Danheiser Unit 3 Stereocontrolled Conjugate Addition Intrinisic Stereochemistry in the Michael Reaction Substrate Control: Asymmetric Induction by Molecular Framework Substrate Control: Asymmetric Induction via Chiral Auxiliaries Catalytic Asymmetric Conjugate Addition I: Unstabilized Nucleophiles Catalytic Asymmetric Conjugate Addition II: Conjugate Reduction Catalytic Asymmetric Conjugate Addition III: Stabilized Nucleophiles (Michael Additions)
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Hayashi-Miyaura Rh-Catalyzed Conjugate Addition Reactions Reviews
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Unformatted text preview: T. Hayashi et al. Chem. Rev . 2003, 103, 2829 and Bull. Chem. Soc. Jpn. 2004, 77, 13 Org. Synth. Coll. Vol. 10, 609 Recent variant using arylzinc compounds: J. Am. Chem. Soc . 2004, 126, 6240 Cu-Catalyzed Conjugate Addition of Organozinc Compounds B. Feringa et al. In Modern Organocopper Chemistry; Krause, N., Ed.; Wiley-VCH, 2002, pp 224-258 O O O PhZnCl 1.5 equiv 7: 98% yield, 99% ee 8: 99% yield, 94% ee H 2 O [RhCl(( R )-binap)] 2 (3 mol% Rh) THF, 20 o C, 1h Ph Ph Me i-Pr + PhZnCl 1.5 equiv H 2 O [RhCl(( R )-binap)] 2 (3 mol% Rh) THF, 20 o C, 1h + O Me i-Pr Figure by MIT OCW...
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