(S)-(-)-1-Amino-2-methoxy-pyrrolidine (SAMP) and (R)-(+)-1-Amino-2-methoxypyrrolidine (RAMP) as Versatile Chiral Auxiliaries

(S)-(-)-1-Amino-2-methoxypyrrolidine (SAMP) and (R)-(+)-1-amino-2-methoxypyrrolidine (RAMP) are commercially available chiral auxiliaries and have been successfully applied to asymmetric synthesis, especially bioactive natural product synthesis. [1] (S)-(-)-1-Amino-2-methoxypyrrolidine (SAMP) and (R)-(+)-1-amino-2-methoxypyrrolidine (RAMP ) emerged as chiral auxiliaries for a-alkylation in various application during the total synthesis of various complex organic molecules. The a-alkylation generally proceeds via the a-alkylation of SAMP/RAMP hydrazones followed by 1,2-addition and reductive N-N bond cleavage. [2]

Recently SAMP/RAMP chiral auxiliaries was efficiently used as chiral auxiliaries in various important reactions, which includes the palladium catalyzed allylic substitution, [3] asymmetric synthesis of substituted b-formyl d-lactones and furofuran lactones, [4] diastereo- and enantioselective synthesis of syn-2,3-disubstituted, 1,4-diketones, [5] diastereoselective electrophillic fluorination of enatiopure a-silylketones, [6] recemization free cleavage of ketones SAMP hydrazones, [7] diastereo-and enantioselective synthesis of various 1,2-anti tert-butyl sulfanyl amines, [8] asymmetric synthesis of g-amino nitriles and g-amino ketones [9] etc.

References

• 1a Enders D. Thiebes C. Pure. Appl. Chem.  2001,  73:  573 
• 1b Enders D. In Asymmetric Synthesis   Morrison J.-D. Academic; New York: 1984.  Vol. 3. p.275 
• 1c Enders D. Klaff M. In Encyclopedia of Reagents for Organic Synthesis   Paquette LA. Wiley; Chichester: 1995.  Vol. 1. p.178 
• 1d Enders D. Fey P. Kipphardt H. Synthesis  1987,  173 
• 2a Enders D. Eichenauer H. Tetrahedron Lett.  1977,  18:  191 
• 2b Enders D. Reinhold U. Tetrahedron: Asymmetry  1997,  8:  1895 
• 2c Enders D. Lochtman R. Meiers M. Muller S. Lazny R. Synlett  1998,  1182 
• 2d Enders D. Thiebes C. Synlett  2000,  1745 
• 2e Enders D. Kirchhoff JH. Synthesis  2000,  2099 
• 3 Mino T. Imiya W. Yamashita M. Synlett  1997,  583 
• 4 Enders D. Vazquez J. Raabe G. Eur. J. Org. Chem.  2000,  893 
• 5 Enders D. Muller P. Klein D. Synlett  1998,  43 
• 6 Enders D. Faure S. Potthoff M. Runsink J. Synthesis  2001,  2307 
• 7 Enders D. Hundertmark T. Lazny R. Synlett  1998,  721 
• 8 Enders D. Schaadt A. Synlett  2002,  498 
• 9 Enders D. Janeck CF. Runsink J. Synlett  2000,  641 
• 10 Enders D. Teschner P. Grobner R. Raabe G. Synthesis  1999,  237 
• 11 Enders D. Kallfass U. Nolte B. Synlett  2002,  1:  33 
• 12 Enders D. Ridder A. Synthesis  2000,  1848 
• 13 Enders D. Nuhring A. Runsink J. Raabe G. Synthesis  2001,  1406