Roxanne Atienza Short Literature Presentation January 24, 2011
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1 Aza-xy-Carbanion elay via on-brook earrangement: Efficient ynthesis of Furo[3,2-c] pyridinones Liang, F.; Lin,.; Wei, Y. J. Am. Chem. oc. 2011, AAP. Double Isocyanide Cyclization: A ynthetic trategy for Two- Carbon-Tethered Pyrrole/xazole Pairs Li, Y.; Xu, X.; Tan, J.; Xia, C.; Zhang, D.; Liu, Q. J. Am. Chem. oc 2010, AAP. oxanne Atienza hort Literature Presentation January 24, 2011
2 Aza-xy-Carbanion elay via on-brook earrangement: Efficient ynthesis of Furo[3,2-c] pyridinones Liang, F.; Lin,.; Wei, Y. J. Am. Chem. oc. 2011, AAP.
3 ortheast ormal University Chemistry n the basis of the former ortheast University, combining with the former Changchun University and Changbai ormal College, the chemistry department of natural science college of EU was founded in ct It was renamed the Chemistry Department of EU in As one of the earlier departments of science established in our university, the Chemistry Department merged with the Analysis & Testing Center to form the Faculty of Chemistry of EU. 29 professors 24 associate professors, 15 doctoral supervisors 32 teachers with doctoral degrees 34 people engaging in the doctoral program
4 Anionic elay Chemistry an anionic functional group resulting from one organic reaction is transferred to a different location within the same carbon framework and available for secondary reactions
5 Initial Idea and ptimization a/et reflux + 77%, 35% 70% % t-buk/t-bu a/dm 80 C 85% or a/tf reflux or a/dmf 80 C 80 C
6 Control eaction to Probe Mechanism a/ DM 80 C 3 C 3 C 82% The bicyclic product is formed when an additional electrophile is T present
7 Proposed Mechanism base aza-michael cyclopropane ring opening /cyclization E+ E Electrophile trapping
8 ubstrate cope Ar' Ar'' aryl groups can be electron-rich or poor + aldehydes include electron rich aryl, electron poor aryl, or heteroaryls a/dm Ar' Ar'' 79-91% 10 examples 3 new bonds in one-pot C- C-C C- Ar 3 C + Ar a/dm 3 C Ar = 88% 4-Cl 85% 2-furyl 81%
9 Double Isocyanide Cyclization: A ynthetic trategy for Two- Carbon-Tethered Pyrrole/xazole Pairs Li, Y.; Xu, X.; Tan, J.; Xia, C.; Zhang, D.; Liu, Q. J. Am. Chem. oc 2010, AAP.
10 Previous Work = (C2)2 Et 2 C 1 C a C 2 Et 1 C22 DBU 1 Et 2 = Et EWG = C 2 EWG = C 1 Bi, X.; Dong, D.; Liu, Q.; Pan, W.; Zhao, L; Li, B. Tan, J.; Xu, X.; Zhang, L.; Li, Y.; Liu, Q. Angew. Chem., Int. Ed. 2009, 48, 2868 EWG J. Am. Chem. oc. 2005, 127, 4578 ' ' C DBU C 2 Et 1 C DBU C 2 Et = (C2)2 EWG = C Et 2 C C C 2 Et C 2 Et 1 = (C2)2 EWG = C 1 Zhang, L.; Xu, X.; Tan, J.; Pan, L.; Xia, W.; Liu, Q. Chem. Commun. 2010, 46, 3357
11 C2-Tethered eterocyclic atural Products C 3 C 3 C 3 iphonazole Br Br C Cyclooroidin Paprotrain 2
12 Initial eaction p-cl tol C 2 eqv. C 2 Et DBU (0.5 eqv) MeC 80 C C 2 Et p-cl C 2 Et tol 84% ' C 2 eqv. C 2 Et C 2 Et ' DBU (0.5 eqv) MeC 80 C C 2 Et 50-89% 12 examples electron rich, electron deficient, aromatic and heteroaromatic groups tolerated
13 Bicyclic Aminal Product tol C 2 eqv. C 2 Et DBU (1.0 eqv) MeC 80 C Et 2 C tol Et 2 C tol ingle Isocyanide Cyclization 61%
14 Isolation of Intermediate Product p-me tol C 2 eqv. C 2 Et tol DBU (0.5 eqv) MeC 25 C, 1h p-me C C 2 Et 31% eaction Intermediate isolated p-me C C 2 Et tol C 1.2 eqv. C 2 Et DBU (0.5 eqv) MeC 25 C, 16h C 2 Et p-me C 2 Et 92% tol e-subjecting to modified reaction conditions leads to product
15 Proposed Mechanism ' C C 2 Et ' ' ' Double Michael Addition [5+1] Et 2 C C Et 2 C C Alkylthio Elimination Et 2 C C Et 2 C C ' loss of thiirane Et 2 C C ' C 1,2 addition C 2 Et C C 2 Et Et 2 C C ' isocyanide cyclization formation of pyrrole C Et 2 C C 2 Et C ' C C 2 Et Et 2 C deprotonation to form thiol ' C C 2 Et Et 2 C deprotonation to form enolate ' C C 2 Et Et 2 C isocyanide cyclization formation of oxazole ' C 2 Et Et 2 C '
16 2 eqv. C 2 Et ' ' C C 2 Et DBU (0.5 eqv) MeC 80 C C 2 Et 50-89% 12 examples 5 ew Bonds Formed 4 C-C 1 C- 2 heterocycles ne-pot
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