By Cotton F., Wilkinson G., Murillo C., Bochmann M.

ISBN-10: 0471199575

ISBN-13: 9780471199571

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Table 12 Synthesis of pyrroles via multicomponent reaction Br NC NC O 2% (Ph3P)2PdCl2 1% CuI, Et3N, ∆ 126 O Ph R NC OH H 20 mol% 54 then R'NH2 HOAc, ∆ XXVII Ph 127 Entry 128 R R’ Yield (%) Entry 128 R 1 2 3 4 Ph 4-OMec6H4 n-Pentyl (CH2)5OH H H H H 70 60 59 53 e f g h a b c d 5 6 7 8 Ph 2-furyl Ph Ph R N R' 128 Ph R’ Yield (%) Bn Bn CH2CO2Et CH2CH2OH 60 55 54 57 104 J. L. Moore, T. Rovis Recently, Hamada and co-workers utilized the Stetter reaction in a cascade sequence to produce dihydroquinolines, of type 131, in excellent yields Eq.

Different proline-derived catalysts have been reported by the Hayashi [338], Córdova [339], Wang [340], and Ley groups [341, 342]. As illustrated in Schemes 33 and 34, catalysts capable of hydrogen bonding or Brønsted acid activation (Type A catalysts) are generally highly effective and enantioselective catalysts for a-oxygenation and a-amination reactions. With nitrosobenzene, type A catalysts have so far been the only successful catalysts. The high reactivity of the reagents and the double activation mode of the catalyst both contribute to extremely high enantioselectivities typically observed in these processes.

This is further evidenced by the observation that the diastereomeric ratio is higher when the reaction is stopped before complete consumption of starting material. Homoenolates generated catalytically with NHCs can also be employed for C-C and C-N bond formation. Bode and Glorius have independently accomplished the diastereoselective synthesis of g-butyrolactones by annulation of enals and aldehydes [121, 122]. Bode and co-workers envisioned that increasing the steric bulk of the acyl anion equivalent would allow reactivity at the homoenolate position.

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Advanced inorganic chemistry by Cotton F., Wilkinson G., Murillo C., Bochmann M.


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