Synlett 2003(11): 1755-1756
DOI: 10.1055/s-2003-41439
SPOTLIGHT
© Georg Thieme Verlag Stuttgart · New York

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

M. Mujahid Alam*
Inorganic Chemistry Division, Indian Institute of Chemical Technology, Hyderabad - 500007. India
Fax: +91(40)27160921; e-Mail: mujahid1206@yahoo.com;
Further Information

Publication History

Publication Date:
22 September 2003 (online)

(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.

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