Recent applications of chiral binaphtholderived phosphoric acid in catalytic asymmetric reactions
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1 Recent applications of chiral binaphtholderived phosphoric acid in catalytic asymmetric reactions 1. Seayad, J.; Seayad, A. M.; List, B. J. Am. Chem. Soc. 2006, ASAP. 2. Storer, R. L.; Carrera, D. E.; Ni, Y.; MacMillan, D. W. C. J. Am. Chem. Soc. 2006,128, Hoffmann, S.; Seayad, A. M.; List, B. Angew. Chem. Int. Ed. 2005, 44, Rowland, G. B.; Zhang, H.; Rowland, E. B.; Chennamadhavuni, S.; Wang, Y.; Antilla, J. C. J. Am. Chem. Soc. 2005,127, Uraguchi, D.; Sorimachi, K.; Terada, M. J. Am. Chem. Soc. 2005,127, Uraguchi, D.; Sorimachi, K.; Terada, M. J. Am. Chem. Soc. 2005,127, Uraguchi, D.; Terada, M. J. Am. Chem. Soc. 2004,126, Akiyama, T.; Itoh, J.; Yokota, K.; Fuchibe, K. Angew. Chem. Int. Ed. 2004, 43, Akiyama, T.; Morita, H.; Itoh, J.; Fuchibe, K. rg. Lett. 2005, 7, R P H R Literature Presentation Zhenjie Lu Jan 12, 2006
2 Introduction Stereoselective chemical transformations perhaps have over emphasized the virtue of metal catalysis but this picture is changing rapidly; fast developing metal-free catalysis with small organic molecules as been described as utilizing artificial enzymes or being enzyme mimetics. advantages of using Bronsted acid a. Metal-free chiral organocatalysts exhibit catalytic activity by themselves. b. rganocatalysts are generally stable in air and easily stored. c. Chiral Bronsted acid catalysts would electrophilically activate C= or C=N bond, and cause chiral induction. Schreiner, P. R. C hem. Soc. Rev. 2003, 32, 289.
3 Chiral Binaphthol-Derived Phosphoric Acid R P H R Plausible hydrophosphonylation mechanism The tetradentate structure around the phosphorus(v) prevent free rotation at the phosphorus center by formation of a ring structure. This cannot be found in other carboxylic and sulfonic Bronsted acids. The appropriate acidity (pka of diethylphosphate is 1.39) should catch up the substrate through hydrogen bonding without loose ion-pair formation. The phosphoryl oxygen should function as a Lewis basic site, and thus a phosphoric acid could function as a bifunctional catalyst. Schreiner, P. R. C hem. Soc. Rev. 2003, 32, 289.
4 I. Bronsted Acid Catalyzed Mannich - type Reaction Bulky Bronsted acid and aromatic solvent gave better selectivity. Akiyama, T.; Itoh, J.; Yokota, K.; Fuchib e, K. Angew. C hem. Int. Ed. 2004, 43, 1566.
5 I. Bronsted Acid Catalyzed Mannich - type Reaction N 2 Akiyama s catalyst and results. P H N 2 Akiyama's catalyst Akiy ama, T.; Itoh, J.; Yokota, K.; Fuchibe, K. Angew. Chem. Int. Ed. 2004, 43, 1566.
6 I. Bronsted Acid Catalyzed Mannich - type Reaction Terada s catalyst and results. P H Terada's catalyst in Mannich reaction Uraguchi, D.; Terada, M. J. Am. C hem. Soc. 2004,126, 5356.
7 II. Bronsted Acid Catalyzed Friedel Crafts - type Reactions a. 0.1 M in (CH 2 Cl) 2 at -35 o C for 24h. Halogenated solvent gave better results than ethereal or aromatic solvents. (87% yield, 97% ee vs. 70% yield, 83% ee in THF or 88% yield, 83% ee in toluene.) Uraguchi, D.; Sorimachi, K.; Terada, M. J. Am. C hem. Soc. 2005,127,
8 II. Bronsted Acid - Catalyzed Friedel Crafts - type Reactions
9 II. Bronsted Acid - Catalyzed Friedel Crafts - type Reactions 3 mol% of 5 toluene, rt, 24h Uraguchi, D.; Sorimachi, K.; Terada, M. J. Am. C hem. Soc. 2005,127, 9360.
10 II. Bronsted Acid Catalyzed Friedel Crafts - type Reactions: Pictet-Spengler Reaction Pictet-Spengler Reaction: R 2! " R 3 R 1 + NH 2 R 4 R 5 Jacobsen s approach protic or lewis acid R 2! " R 3 R 1 N R 5 R 4 R 1 NH! " R 3 R 2 R 4 R 5 tetrahydroisoquinoline List s approach R' R'' X chiral thiourea N R catalyst -HX 1) Taylor, M. S.; Jacobsen, E. N. J. Am. C hem. Soc. 2004, 126, ) Seayad, J.; Seayad, A. M.; List, B. J. Am. C hem. Soc. 2006, ASAP.
11 II. Bronsted Acid Catalyzed Friedel Crafts - type Reactions: Pictet-Spengler Reaction P H 5 List's catalyst This reaction tolerates aromatic aldehydes (at -10 o C in CH 2 Cl 2 ) (entry 12-16). Seayad, J.; Seayad, A. M.; List, B. J. Am. Chem. Soc. 2006, ASAP.
12 III. Bronsted Acid Catalyzed Reductive Amination Catalytic asymmetric hydrogenation to imine is limited. Rueping s approach: Proposed mechanism (HEH) CF 3 CF 3 P H CF 3 CF 3 Rueping, M.; Sugiono, E.; Azap, C.; Theissmann, T.; Bolte, M. rg. Lett. 2005, 7, 3781.
13 III. Bronsted Acid Catalyzed Reductive Amination Rueping s approach: N PMP R CH 3 R = Ar, 46-91% yield, 70-82% ee. List s approach: N PMP HEH, 20mol% A1 benzene, 60 o C HEH, 1 mol% A2 toluene, 35 o C HN PMP R CH 3 HN PMP A R P H R Rueping's A1: R = 3,5-(CF 3 )-phenyl List's A2: R = 2,4,6-()-phenyl MacMillan's A3: R = SiPh 3 R CH 3 R CH 3 R = Ar,, 80-98% yield, 80-93% ee. ne example that from ketone to a deprotected amine (R = Ph, 75% overall yield, 88% ee). MacMillan s approach: + R CH 3 NH 2 R' HEH, 10 mol% A3 5 A MS, o C benzene, 24-96h HN R CH 3 R' R = Ar, R = Me, 60-87% yield, 83-95% ee. R = alkyl, R = Me, 49-75% yield, 81-94% ee. R = Ar, R = aryl, 55-92% yield, 91-95% ee. 1) Ruep ing, M.; Sugiono, E.; Azap, C.; Theissmann, T.; Bolte, M. rg. Lett. 2005, 7, ) Hoffmann, S.; Seayad, A. M.; List, B. Angew. Chem. Int. Ed. 2005, 44, ) Storer, R. L.; C arrera, D. E.; Ni, Y.; MacMillan, D. W. C. J. Am. C hem. Soc. 2006,128, 84.
14 IV. Bronsted Acid Catalyzed Hydrophosphonylation Akiyama, T.; Morita, H.; Itoh, J.; Fuchibe, K. rg. Lett. 2005, 7, 2583.
15 V. Bronsted Acid Catalyzed Imine Amidation catalyst A: 91-99% yield, catalyst B: 91-99% yield. Rowland, G. B.; Zhang, H.; Rowland, E. B.; C hennamadhavuni, S.; W ang, Y.; Antilla, J. C. J. Am. Chem. Soc. 2005,127,
16 Bronsted Acid - Catalyzed Imine Amidation Toluene was used as solvent in entry Rowland, G. B.; Zhang, H.; Rowland, E. B.; C hennamadhavuni, S.; W ang, Y.; Antilla, J. C. J. Am. Chem. Soc. 2005,127,
17 Conclusion N 2 anth P H P H P H anth Akiyama - Mannich N 2 Terada - alkylation of diazoester Ph Ph Si Ph Terada - Mannich R P H P H P H Si Ph Ph Ph MacMillan - amination CF 3 R Terada - aza-friedel-crafts CF 3 P H CF 3 P H Ph Ph P H CF 3 Rueping - amination and Akiyama - hydrophosphonylation List - Pictet-Spengler and amination Antilla -imine amidation
18 Bronsted Acid - Catalyzed Mannich-type Reaction- Deastereoselectivity N 2 P H N 2 Akiyama's catalyst Akiy ama, T.; Itoh, J.; Yokota, K.; Fuchibe, K. Angew. Chem. Int. Ed. 2004, 43, 1566.
19 Bronsted Acid - Catalyzed Friedel Crafts - type Reactions Pictet-Spengler Reaction Jacobsen s approach 1) Taylor, M. S.; Jacobsen, E. N. J. Am. C hem. Soc. 2004, 126, ) Seayad, J.; Seayad, A. M.; List, B. J. Am. C hem. Soc. 2006, ASAP.
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