Stereoselective Synthesis of Configurationally Stable Functionalized Ethano-Bridged Tröger Bases
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1 Stereoselective Synthesis of Configurationally Stable Functionalized Ethano-Bridged Tröger Bases Michon, C.; Sharma, A.; Bernardinelli, G.; Francotte, E.; Lacour, J. Chem. Commun., 2010, 46, ne-step Catalytic Asymmetric Synthesis of Configurationally Stable Tröger Bases Sharma, A.; Guénée, L.; aubron, J-V; Lacour, J. Angew. Chem. Int. Ed. 2011, 50,
2 Jérome Lacour 1993:.D. University of Texas at Austin (ilip D. Magnus) : Postdoctoral Fellow, arvard University (David A. Evans) 1995: Joined the University of Geneva 2001: Sandoz Family Foundation professorship 2004-current: Full professor esearch Interests rganometallic reactivity and asymmetric transformations (enantioselective C C, C, and C reactions; Ion pari driven asymmetric processes Synthetic, physical and biological applications of highly stable (chiral) carbenium ions M enantiodifferentiation of chiral substances Stereoselective synthesis by asymmetric induction onto configurationally labile (and stable) molecules ew chiral auxiliaries and ligands using hexacoordinated phosphorus chemistry
3 What is a Tröger Base? First prepared in 1887 by Julius Tröger C Eisner and Wagner proposed a different structure C C Spielman 1935: a) o reaction with phenyl isocyanate or phenyl mustard oil b) o reduction with metals Spielman, M. A. JACS 1935, 57,
4 Proposed chanism for the Tröger Base + Cl MTA 2 DMS or MTA Cl S S Cl 2 S Cl 2 S S 2 S
5 More on Tröger Bases methano-bridged tröger base ethano-bridged tröger base Stereogenic nitrogen due to conformational strain Enantiomers first separated in 1944 by Vladimir Prelog Facile racemization of compounds under acidic/basic conditons ot to many applications as enantiopure ligands or auxiliaries Diethylzinc addition to aldehydes (up to 86% ee) Conversion of methano-bridged to ethanobridged avoids racemization my iminium Prelog, V.; Wieland, P. elvetica Chimica Acta 1944, 27, armata, M.; Kahraman, M. Tetrahedron: Asymmetry, 2000, 11,
6 Stereoselective Synthesis of Configurationally Stable Functionalized Ethano-Bridged Tröger Bases [1,2]-Stevens earrangement base chanism B nitrogen ylide C 2 C 2 C 2
7 [1,2]-Stevens earrangement with Tröger bases Br!, C 6 6 C 2 87% yield a a C 2 b b Entry Base Equiv b : a % yield 1 DABC 5 36 : Et : Proton sponge 5 27 : Et(i-Pr) : Al 2 3 (p= 9.5 ±0.5) : Al 2 3 (p= 9.5 ±0.5) : 11 85
8 Substrate Scope X Y X Y C 2 Y X Al 2 3 (p 9.5) CCl 3, 2 h 25 C Y X 85% yield >98:2 dr 51% yield >98:2 dr 34% yield >98:2 dr F Br 65% yield >98:2 dr 40% yield >98:2 dr 35% yield >98:2 dr
9 acemization Test/Transformation Stirred in or CCl3 for 2 hr at 23 C and 60 C no loss of ee Stirred in or CCl3 for 2 hr at 23 C and 60 C with 2 equivalents of camphorsulfonic acid no loss of ee 99% ee Stirred in DMF for 2 hr at 100 C with 2 equivalents of camphorsulfonic acid loss to 88% ee 1) ab 4 or 2) Li Felkin-Anh addition 87-97% yield dr >49:1
10 ne-step Catalytic Asymmetric Synthesis of Configurationally Stable Tröger Bases General Concept h 2 (Ac) 4, 100 C 1 2 [1,2]-Stevens rearrangement 1 2 Control the diastereoselectivity? Chirality transfer?
11 Diastereoselectivity ptimization h 2 (Ac) 4, 100 C 1 2 Entry 1 2 d.r. % yield 1 C C 2 C2Et C2Et 85 3 C2Et C 2: C 5: C2Et >49: C2 10:1 75
12 X Substrate Scope/Chirality Transfer X 1 X 2 h 2 (Ac) 4, 100 C 1 X 99% ee C 2 C 2 C 2 C 2 71% yield 10:1 dr 99% ee 70% yield 8:1 dr 98% ee 83% yield 10:1 dr 98% ee F 3 C 2 C 2 C 2 C 2 70% yield 12:1 dr 97% ee 82% yield 20:1 dr 64% ee 89% yield 16:1 dr 97% ee
13 chanistic ationale h h 1 C 2 1 C 2 1 or C 2 1 C 2 1 C 2
14 Control of egioselectivity Et 2 C C 2 Et 2 2 h 2 (Ac) 4, 100 C Et 2 C 2 71% yield Single egioisomer C 2 Et 2 1 C 2
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