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4_11_05 - Massachusetts Institute of Technology Organic...

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Massachusetts Institute of Technology Organic Chemistry 5.512 April 11, 2005 Prof. Rick L. Danheiser Unit 4 Stereocontrolled 1,2-Addition to Carbonyl Groups l i l iti i Al l l l l l l Addition of "Unstabilized" Carbon Nucleophiles Reagent Contro : Organoz nc and Re ated Add on React ons ky , A keny , and A kyny Meta Compounds General Reviews on Organozinc Chemistry "Preparation and Applications of Functionalized Organozinc Compounds" Knochel, P.; Millot, N.; Rodriguez, A. L.; Tucker, C. E. Organic Reactions 2001 , 58 , 417-731 "Organozinc Reagents: A Practical Approach" Knochel, P.; Jones, P.; Oxford, 1999 3 SiCl 2 2 Li l 2 i 2 R 2 + 2 Z vola e) + 2 2 2 + iv 2 ( ) R 2 + 3 vola e) General Methods for the Preparation of Organozinc Compounds Oxidative Addition R-I Zn, Me BrCH CH Br THF or Naph, ZnC R-ZnI Halogen-Zinc Exchange Transmetalation R-I 2-5 equ v Et Zn cat CuI or CuCN Zn EtI, Et n ( til RLi or RMgX ZnBr or ZnCl R-ZnX R-BEt 2 equ Et Zn , rt neat Zn Et B ( til
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Asymmetric Addition of Dialkylzinc Compounds to Aldehydes Review: "Catalytic Asymmetric Organozinc Additions to Carbonyl Compounds"
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