a b b c a c Ally anion type Propargyl/allenyl anion type a b c a b c a b c a b c a b c a b c b =,, or C a b c a b c b = Gothelf, K. V.; Jørgensen, K.

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2 a b b c a c Ally anion type Propargyl/allenyl anion type a b c a b c a b c a b c a b c a b c b =,, or C a b c a b c b = Gothelf, K. V.; Jørgensen, K. A. Chem. ev. 1998, 98,

3 itrogen in the middle Allyl anion type xygen in the middle Propargyl/allenyl anion type itrillium Betaines C itrone C Carbnyl xides C itrile xides C Azomethine Imines C Carbonyl Imines C itrile Imines C C Azomethine Ylides C C Carbonyl Ylides C C itrile Ylides Azimines itrosimines Diazonium Betaines Azoxy Compounds itrosoxides itrous xide itro Compounds zone Azides C Diazoalkenes Gothelf, K. V.; Jørgensen, K. A. Chem. ev. 1998, 98,

4 a b b c a c a b b c a b c a c Ar C D D D Ar D Gothelf, K. V.; Jørgensen, K. A. Chem. ev. 1998, 98,

5 Dipole Alkene Dipole Alkene Dipole Alkene LUM M Type I Type II Type III C C C C C Gothelf, K. V.; Jørgensen, K. A. Chem. ev. 1998, 98,

6 Dipole Alkene Alkene- Lewis acid Dipole- Lewis acid Dipole Alkene LUM M Type I Type III Gothelf, K. V.; Jørgensen, K. A. Chem. ev. 1998, 98,

7 Dipole Dipolarophile Dipolarophile- Lewis acid Dipole- Lewis acid Dipole Alkene LUM M LA Lewis acid 2 Lewis acid 2 LA X X 1 1 Stanley, L. M.; Sibi, M. P. Chem. ev. 2008, 108,

8 endo (trans) exo (cis) 3 4 Endo-transition state for the Diels-Alder reaction X X Transition state for 1,3-dipolar cycloaddition 1 X 1 endo 2 exo 2 Gothelf, K. V.; Jørgensen, K. A. Chem. ev. 1998, 98,

9 endo (trans) exo (cis) isoxazolidine eduction 2 /Pd 2 /aney i Zn, acid and more β-amino alcohol 2 1 is removed in eduction step primary amine Gothelf, K. V.; Jørgensen, K. A. Chem. ev. 1998, 98,

10 endo (trans) exo (cis) Pellissier,. Tetrahedron 2007, 63,

11 3 C e-face PMP Si-face 3 C PMP 3 C Toluene, 110 C PMP 3 C C 3 e-face PMP Si-face Ar 3 C endo-approach exo-approach PMP 3 C PMP major 2; =Bn : 95% (dr=100:0:0:0) 3; = : 80% (dr=73:9:9:9) Alcaide, B.; Almendros, P.; Alonso, J. M.; Aly, M. F.; Pardo, C.; Sáez, E. Torres, M.. J. rg. Chem. 2002, 67,

12 t-bu 3 C 2 C tbu 4 C 2 C 3 toluene, 60 C, 1 day, 77% 5 6 sole adduct tbu 3 C 2 C 3 C 2 C 6 tbu 1) MsCl, TEA 2) 2, Pd/C 3 C 2 C tbu 8 enantiopure indolizidine Cordero, F. M.; Pisaneschi, F.; Gensini, M.; Goti, A.; Brandi, A. Eur. J. rg. Chem. 2002,

13 Ac Ac Ac Ac t-bu Ac t-bu Ac t-bu Ac Ac 9; 81%; de = 100% 4 10; 62%; de = 100% AcAc t-bu Ac Ac Stecko, S.; Paśniczek, K.; Jurczak, M.; Urbańczyk-Lipkowska, Z.; Chmielewski, M. Tetrahedron: Asymmetry 2006,

14 Cl, ac Cl, ac Shing. T. K. M.; Zhong, Y. L. Tetrahedron 2001, 57,

15 Cl, ac = Shing. T. K. M.; Zhong, Y. L. Tetrahedron 2001, 57,

16 Cl, ac Shing. T. K. M.; Zhong, Y. L. Tetrahedron 2001, 57,

17 Cl Cl Co(III)-SbF 6 (5 mol%) -40 C, C 2 Cl 2 60 h, quant. ab 4 Et Ar endo:exo= >99:1 87% ee (endo) Co SbF 6 Co(III)-SbF 6 Mita, T.; htsuki,.; Ikeno, T.; Yamada, T. rg. Lett. 2002, 15,

18 Cl Cl favored Co(III)-SbF 6 (5 mol%) Ar Co -40 C, C 2 Cl 2 60 h, quant. Ar Ar Ar Ar ab 4 Et Ar 18 endo:exo= >99:1 87% ee (endo) Ar disfavored (S) () (S) (S) Ar endo adduct Ar endo adduct Mita, T.; htsuki,.; Ikeno, T.; Yamada, T. rg. Lett. 2002, 15,

19 Bn Cl 4 20 mol% Bn C Bn C 70% (endo:exo=99:1) 99% ee (endo) e-face Bn C Bn 21 endo Jen, W. S.; Wiener, J. J. M.; MacMillan, D. W. C. J. Am. Chem. Soc. 2000, 122,

20 10 mol% Cl DMF- 2, -10 C 120 h ab 4 C 2 C 2 24 endo 25 exo 50% (exo:endo=97:3) 90% ee (exo) C C 24 endo C 25 exo Karlsson, S.; ögberg,. Eur. J. rg. Chem. 2003,

21 Cl ab 4 DMF- 2, -10 C 120 h attack from sterically lowest hindered side attack from sterically hindered side C 2 C 2 24 endo 25 exo s-cis s-trans s-cis s-trans 2Cl 2Cl 2Cl 2Cl nitrone nitrone nitrone nitrone (E)-iminium isomers (Z)-iminium isomers Karlsson, S.; ögberg,. Eur. J. rg. Chem. 2003,

22 22

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