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1 Topic Review Group meeting Memory of chirality Christian Gloor Based on: Zhao, H.; Hsu, D. C.; Carlier, P.R. Synthesis 2005,1, 1.
2 Table of content > Definitions of memory of chirality > Types of chirality > Requirements for memory of chirality > Memory of chirality in enolate chemistry > Memory of chirality in radical chemistry > Memory of chirality involving carbocation intermediates > Conclusion 25. October
3 Definitions of memory of chirality > Central chirality at a carbon alpha to a carbonyl group is preserved as transient axial chirality of the intermediate enolate and is then regenerated as central chirality in the reaction product (memory of chirality). 1 > The chirality of the starting ti material is preserved in a reactive intermediate t for a limited time. 2 > The chirality of a starting material having a chiral sp 3 -carbon is preserved in the reaction product even though h the reaction proceeds at the chiral carbon as a reaction center through reactive intermediates such as carbanion, singlet monoradicals, biradicals, or carbenium ions. 3 1 Kawabata, T.; Yahiro, K.; Fuji, K. J. Am. Chem. Soc. 1991,113, Fuji, K.; Kawabata, T. Chem. Eur. J. 1998, 4, Wanyoike, G. N.; Onomura, O.; Maki, T.; Matsumura, Y. Org. Lett. 2002, 4, October
4 Types of Chirality > Dynamic chirality is not a sufficient condition for MOC since the intermediate t has to be formed enantioselectively. l 1 Fuji, K.; Kawabata, T. Chem. Eur. J. 1998, 4, October
5 Requirements for memory of chirality > The three requirements for memory of chirality are: 1 1 Zhao, H.; Hsu, D.C.; Carlier, P.R. Synthesis 2005, 1, October
6 Memory of chirality in enolate chemistry > Seebach, D.; Wasmuth, D. Angew. Chem. 1981, 93, > Zhao, H.; Hsu, D. C.; Carlier, PR P.R. Synthesis 2005, 1, October
7 Memory of chirality in enolate chemistry > Kawabata, T.; Yahiro, K.; Fuji, K. J. Am. Chem. Soc. 1991, 113, October
8 Memory of chirality in enolate chemistry > Kawabata, T.; Yahiro, K.; Fuji, K. J. Am. Chem. Soc. 1991, 113, October
9 Memory of chirality in enolate chemistry > Kawabata, T.; Yahiro, K.; Fuji, K. J. Am. Chem. Soc. 1991, 113, October
10 Memory of chirality in enolate chemistry > Kawabata, T.; Suzuki, H.; Nagae, Y; Fuji, K. Angew. Chem. Int. Ed. 2000, 39, October
11 Memory of chirality in enolate chemistry > Kawabata, T.; Suzuki, H.; Nagae, Y; Fuji, K. Angew. Chem. Int. Ed. 2000, 39, October
12 Memory of chirality in enolate chemistry > Kawabata, T.; Kawakami, S.; Fuji, K. Tetrahedron Lett. 2002, 43, October
13 Memory of chirality in enolate chemistry > Kawabata, T.; Kawakami, S.; Majumdar, S. J. Am. Chem. Soc. 2003,125, October
14 Memory of chirality in enolate chemistry > Kawabata, T.; Kawakami, S.; Majumdar, S. J. Am. Chem. Soc. 2003,125, October
15 Memory of chirality in enolate chemistry > Zhao, H.; Hsu, D. C.; Carlier, P.R. Synthesis 2005,1, 1. > Vohra, S. et al. J. Chem. Soc. Perkin Trans , October
16 Memory of chirality in enolate chemistry > Zhao, H.; Hsu, D. C.; Carlier, P.R. Synthesis 2005,1, 1. > Vohra, S. et al. Chem. Commun. 1998, October
17 Memory of chirality in enolate chemistry > Bonache, M a, A. Et al. Tetrahedron Asymmetry 2003, 14, October
18 Memory of chirality in enolate chemistry > Bonache, M a, A. et al. Tetrahedron Asymmetry 2003, 14, October
19 Memory of chirality in enolate chemistry > Carlier, P. R. et al. JACS 2003, 125, October
20 Memory of chirality in complex chemistry > Schmalz, H.-G.; Koning, C.B.S.; Bernicke, D.; Siegel, S.; Pfletschinger, A. Angew. Chem. Int. Ed. 1999, 38, October
21 Retentive radical trapping controlled by a slow ring inversion > Buckmelter, A.J.; Powers, J.P.; Rychnovsky, S.D. J. Am. Chem. Soc. 1998, 120, October
22 Retentive radical trapping controlled by a slow ring inversion > Buckmelter, A.J.; Powers, J.P.; Rychnovsky, S.D. J. Am. Chem. Soc. 1998, 120, October
23 Retentive radical trapping controlled by a slow ring inversion > Buckmelter, A.J.; Kim, A.I.; Rychnovsky, S.D.J. Am. Chem. Soc. 2000, 122, October
24 Retentive radical trapping controlled by a slow ring inversion > Buckmelter, A.J.; Kim, A.I.; Rychnovsky, S.D.J. Am. Chem. Soc. 2000, 122, October
25 Memory of chirality in radical cyclisation > Dalgard, J.E.; Rychnovsky, S.D. Org. Lett. 2004, 6, October
26 Memory of chirality in radical cyclisation > Dalgard, J.E.; Rychnovsky, S.D. Org. Lett. 2004, 6, October
27 Memory of chirality in radical cyclisation > Curran, D.P.; Liu, W.; Chen, C.H.-T. J. Am. Soc. 1999, 121, October
28 Memory of chirality in radical cyclisation > Curran, D.P.; Liu, W.; Chen, C.H.-T. J. Am. Soc. 1999, 121, October
29 Memory of chirality in radical cyclisation > Curran, D.P.; Liu, W.; Chen, C.H.-T. J. Am. Soc. 1999,, 121,, October
30 Memory of chirality in radical cyclisation > Curran, D.P.; Chen, C.H.-T.; Geib, S.J.; Lapierre, A.J.B. Tetrahedron 1999, 60, October
31 Memory of chirality in radical cyclisation > Curran, D.P.; Chen, C.H.-T.; Geib, S.J.; Lapierre, A.J.B. Tetrahedron 1999, 60, October
32 Memory of chirality in radical cyclisation > Giese, B. et al. Angew. Chem. Int. Ed. 1999, 38, October
33 Memory of chirality involving carbocation intermediates > Wanyoike, G. N.; Onomura, O.; Maki, T.; Matsumura, Y. Org. Lett. 2002, 4, October
34 Memory of chirality involving carbocation intermediates > Wanyoike, G. N.; Onomura, O.; Maki, T.; Matsumura, Y. Org. Lett. 2002, 4, October
35 Memory of chirality involving carbocation intermediates > Wanyoike, G. N.; Onomura, O.; Maki, T.; Matsumura, Y. Org. Lett. 2002, 4, October
36 Memory of chirality involving carbocation intermediates > Wanyoike, G. N.; Onomura, O.; Maki, T.; Matsumura, Y. Org. Lett. 2002, 4, October
37 Conclusion > Memory of chirality is an emerging strategy for enantioselective synthesis > To date, most MOC experiments were carried out in enolate chemistry, but MOC is also performed in radical chemistry and with involvement of carbocations as reactive intermediates. > Three conditions have to be fulfilled for MOC: > The chiral starting material must be transformed in a conformationally chiral intermediate > The intermediate must not racemize during the timescale of the reaction > The reaction from the reactive intermediate has to work with a high ee. 25. October
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