Talk:Todd:Catalytic, Asymmetric Pictet-Spengler Reaction

Use this page for discussion. Preface questions/comments with initials. Reply to questions but don't delete the question. If things are resolved, move them to the "resolved" section at the bottom of the page.

General Comments

MHT - Jan19 - the page is quite long. We could consider splitting into sections if anyone is having a browser problem, but otherwise we keep as-is. Much more convenient having everything on one page.

Papers that are relevant and need to be included for the first time

These papers are relevant and have not yet been included. They need a summary paragraph and possibly a scheme

None currently

Papers that have not yet been included, but have been referenced by others

These papers need to be checked for relevance. They typically have come from other, relevant papers, but the relevance may not be clear. If they are relevant and need including, move the citation from this section to the "needs to be included" section on this page. If you wish to then actually include it in the review, write "your initials - doing" next to the paper

Check suitability of "items arising" from the 2004 Terada and Akiyama papers

Items arising from Akiyama and Terada papers: More on early work:

Akiyama (2004) says these earlier reports "claim" the use of chiral B acids:

• C. Palomo, M. Oiarbide, J. M. Garcia, A. Gonzalez, A. Lecumberri, A. Linden, J. Am. Chem. Soc. 2002, 124, 10288
• N. T. McDougal, S. E. Schaus, J. Am. Chem. Soc. 2003, 125, 12094
• Y. Huang, A. K. Unni, A. N. Thadani, V. H. Rawal, Nature 2003, 424, 146.

Akiyama (2004) also mentions these "metal salt" versions:

• J. Inanaga, Y. Sugimoto, T. Hanamoto, New J. Chem. 1995, 19, 707
• H. Furuno, T. Hanamoto, Y. Sugimoto, J. Inanaga, Org. Lett. 2000, 2, 49

Previous Bronsted acid example from Terada

• Schreiner, P. R. Chem. Soc. ReV. 2003, 32, 289.
• Huang, Y.; Unni, A. K.; Thadani, A. N.; Rawal, V. H. Nature 2003, 424, 146.
• McDougal, N. T.; Schaus, S. E. J. Am. Chem. Soc. 2003,125, 12094.

Some other chiral charged Brønsted acid catalysts were reported, see:

• Nugent, B. M.; Yoder, R. A.; Johnston, J. N. J. Am. Chem. Soc. 2004,126, 3418.

Jacobsen Strecker and Mannich history, from Terada

• Sigman, M. S.; Jacobsen, E. N. J. Am. Chem. Soc. 1998, 120, 4901.
• Vachal, P.; Jacobsen, E. N. Org. Lett. 2000, 2, 867.
• Sigman, M. S.; Vachal, P.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2000, 39, 1279.
• Su, J. T.; Vachal, P.; Jacobsen, E. N. AdV. Synth. Catal. 2001, 343, 197.
• Vachal, P.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 10013.
• Wenzel, A. G.; Lalonde, M. P.; Jacobsen, E. N. Synlett 2003, 1919.
• Wenzel, A. G.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 12964.

See also:

• Okino, T.; Hoashi, Y.; Takemoto, Y. J. Am. Chem. Soc. 2003, 125, 12672.
• Okino, T.; Nakamura, S.; Furukawa, T.; Takemoto,Y. Org. Lett. 2004, 6, 625.

Copper complex example from Terada:

• Marigo, M.; Kjærsgaard, A.; Juhl, K.; Gathergood, N.; Jørgensen, K. A. Chem.- Eur. J. 2003, 9, 2359.

(end of items arising)

Papers to Summarise/Check for Suitability

Enantioselective/Lewis Acids:

• Hino, T.; Nakagawa, M. Heterocycles 1998, 49, 499-531.
• Leighton Angew 2009

Enantioselective/Bronsted Acids:

The strengths of these chiral phosphoric acids is governed by: Akiyama Chem Rev 2007 Terada ChemComm 2008 Reviews: a) S.J. Connon, Angew. Chem. Int. Ed. 2006, 45, 3909–3912 b) T. Akiyama, J. Itoh, K. Fuchibe, Adv. Synth. Catal. 2006, 348, 999 – 1010 c) M. S. Taylor, E. N. Jacobsen, Angew. Chem. Int. Ed. 2006, 45, 1520–1543 d) Connon, S. J. Org. Biomol. Chem. 2007, 5, 3407–3417 e) Terada Synthesis 2010, 1929-1982 f) List, Top. Curr. Chem. 2010, 291, 395-456 g) Rueping Angewandte 2011, 50, 6706-6720

Enantioselective/Organocatalysts: Jacobsen 2007 JACS, 129, 13404

Diastereoselective (note: must be catalytic):

• Czarnocki, Z.; MacLean, D. B.; Szarek, W. A. Can. J. Chem. 1986, 64, 2205-2210.
• Czarnocki, Z.; Suh, D.; MacLean, D. B.; Hultin, P. G.; Szarek, W. A. Can. J. Chem. 1992, 70, 1555-1561.
• Czarnocki, Z.; Mieckzkowsi, J. B.; Kiegiel, J.; Arazn ́y, Z. Tetrahyedron: Asymmetry 1995, 6, 2899-2902.
• Tsuji, R.; Nakagawa, M.; Nishida, A. Tetrahedron: Asymmetry 2003, 14, 177- 180.

Smaller items to do

KAB - Jan21 - The scheme for 2009 Hiemstra with the H8-BINOL phosphoric acid in the box, doesn't have the H8-BINOL phosphoric acid in the box. Still has the BINOL.

Resolved

-- 1. KAB attempt to understand 2000 Koomen OrgLett

The figure for Table 1 gives diasteromeric ratios. Where are the diastereomers? I only the possibility for enantiomers in the product. Where's the other stereogenic centre?

They also mentioned "hydrolysis of the starting material" numerous times. I'm assuming they mean hydrolysis of the N-S bond (there doesn't seem any other reasonable place for hydrolysis of the SM to occur), but I just wanted to check. This comment resolved since this paper no longer included in the review. --