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SUMMARY:When Asymmetric Aminocatalysis Meets the Vinylogy Principle
DTSTART:20130320T171500
DTEND:20130320T183000
DTSTAMP:20260916T043444Z
UID:c698122dda629f2c8fdcc1dd3006dff3dd562b9f152668f375dc312d
CATEGORIES:Conferences - Seminars
DESCRIPTION:Prof. Paolo Melchiorre\, ICIQ - Institute of Chemical Research
  of Catalonia\, Tarragona (Spain)\nICREA - Institució Catalana de Recerca
  i Estudis Avançats\, Barcelona (Spain)\nWhen Asymmetric Aminocatalysis M
 eets the Vinylogy Principle\nPaolo Melchiorre\nICIQ - Institute of Chemica
 l Research of Catalonia\, Tarragona (Spain)\nICREA - Institució Catalana 
 de Recerca i Estudis Avançats\, Barcelona (Spain)\ne-mail: pmelchiorre@ic
 iq.es\nAsymmetric aminocatalysis  has greatly expanded the chemist’s ab
 ility to stereoselectively functionalise unmodified carbonyl compounds. Th
 e field has coalesced around two pioneering studies\, \,  which recognize
 d that chiral amines could activate carbonyl compounds according to fundam
 ental and general reactivity concepts: the LUMO-lowering effect\, which is
  the underlying activation principle of iminium ion catalysis\,2 and the H
 OMO-raising effect inherent to enamine catalysis.3 Those activation modes 
 account for the functionalisation of carbonyls at their  and  positi
 ons\, respectively. The successful marriage of these reactivity concepts t
 o the principle of vinylogy  has recently led to the development of novel
  aminocatalytic activation modes\, which allow for the direct\, stereosele
 ctive\, and site-selective functionalization of unsaturated carbonyls at r
 emote positions\, such as the  and even the   positi
 ons.\nHere\, some recent contributions from our laboratories are presented
 . \nFigure 1. Established activation modes in aminocatalysis and the viny
 logous iminium ion strategy\n. (a) List\, B.\; Angew. Chem.\, Int. Ed. 201
 0\, 49\, 1730-1734. (b) Barbas\, C. F. III\; Angew. Chem.\, Int. Ed. 2008\
 , 47\, 42-47. (c) Melchiorre\, P.\; Marigo\, M.\; Carlone\, A.\; Bartoli\,
  G. Angew. Chem.\, Int. Ed. 2008\, 47\, 6138-6171.\n. Ahrendt\, K. A.\; Bo
 rths\, C. J.\; MacMillan\, D. W. C. J. Am. Chem. Soc. 2000\, 122\, 4243–
 4244.\n. List\, B.\; Lerner\, R. A.\; Barbas C. F. III\, J. Am. Chem. Soc.
  2000\, 122\, 2395–2396.\n. a) Fuson\, R. C. Chem. Rev. 1935\, 16\, 1–
 27\; b) Arceo\, E.\; Melchiorre\, P. Angew. Chem.\, Int. Ed. 2012\, 51\, 5
 290-5292.\n. For the seminal study: S. Bertelsen\, M. Marigo\, S. Brandes\
 , P. Dinér\, K. A. Jørgensen\, J. Am. Chem. Soc. 2006\, 128\, 12973–12
 980.\n. For the landmark report: Jia\, Z. J.\,Jiang\, H.\; Li\, J.-L.\; Gs
 chwend\, B.\; Li\, Q.-Z.\; Yin\, X.\; Grouleff\, J.\; Chen\, Y.-C. Jørgen
 sen\, K. A.\; J. Am. Chem. Soc. 2011\, 133\, 5053–5061.\n. (a) Bencivenn
 i\, G.\; Galzerano\, P.\; Mazzanti\, A.\; Bartoli\, G.\; Melchiorre\, P. P
 roc. Natl. Acad. Sci. U.S.A.\, 2010\, 107\, 20642–20647. (b) Bergonzini\
 , G.\; Vera\, S.\; Melchiorre\, P. Angew. Chem.\, Int. Ed. 2010\, 49\, 968
 5–9688. (c) Xu\, T.\; Liu\, Y.\; Melchiorre\, P. Angew. Chem.\, Int. Ed.
  2012\, 51\, 6439-6442.
LOCATION:UNIL\, Génopode\, auditorium B https://planete.unil.ch/plan/?loc
 al=GEN-2006
STATUS:CONFIRMED
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