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Entry Diene Epoxide F'roducta) Yieldh' (70) 86 60" 64 90 5 H 47 a) Elemental analysis, mass spectra, 'H NMR, I3C NMR, and FTIR were all consistent with the indicated formulation. b) Isolated yields. c) Yield was based on amount of active magnesium. d) A 1 : 1 mixture of diastereomers as determined by 'H NMR. 7 Synthesis of y-Lactams from Conjugated Diene-Magnesium Reagents y-Lactams are important intermediates in synthetic routes to five-membered heterocyclic compounds. 2 Rirkr Mognesium, Colciurn, Strontium, rznd Bririiinz 21 foundly important family of biologically active secondary metabolites, many of which have potential uses in medicine and agriculture 1431.
Likewise, the generation of a quaternary center and the incorporation of both a hydroxyl and a carboxyl group required for lactonization are achieved in one synthetic procedure. An example of the formation of a spiro y-lactone from the corresponding 1,2-bk(methy1ene)cyclohexane-magnesium complex is shown in Schcme 1-8. 2adduct, 2, resulting from the incorporation of one molecule of acetone with thc diene complex. -position. Upon warming, the 1,2adduct can further undergo a nucleophilic addition to a second electrophile.
4 Orgtrtiocoppel- Reagents Utilizing Rirkr Copper Table 1-21. Kcnctions of activated copper with alkyl halidcs. 3 CLII-PBU~ CUI-PBLI~ Cut-PRu3 CuI-P(OEt)? CuI-PPhj CuI-P(CHzNMe2)3 Cul-DIPHOS CuBr-PBu3 CuBrSMez CuCN CuCN-PEt3 CUCN-PEt3 CUCN-PBU~ CuCN-P(OEt)3 CuCN-Bipy CUI-PBU~ CUI-PBU~ CUI-PB~3 Cul-PBu3 CUI-PBU~ Cul-PRu3 CUT-PPh? Cul-PPh3 Cu-(NMeZ) Cul-PCy3 CuLPCyl(CHZ)2NMe2 CUI-P(CH~NMC~)~ CulLiSCN CUCN-PBu~ CuCNLi(2-thienyl) CuCN(LiBr):! CuCN(LiBr)z CuSCN(LiBr)2 Cul-PRu3 CUI-PBu~ CUI-PBU~ CUT-PBu?