Citation: Song Qing WANG, Omar A. ffiRAHIMI, Pan LI, Kang ZHAO. N-Alkoxyl Templates for Diastereoselective Pyrrolidine Synthesis[J]. Chinese Chemical Letters, ;2004, 15(1): 1-4. shu

N-Alkoxyl Templates for Diastereoselective Pyrrolidine Synthesis

1.
College of Pharmaceuticals and Biotechnology, Tianjin University, Tianjin 300072;
2.
Department of Chemistry, New York University, New York, NY 10003, USA

Received Date: 15 November 2002

Fund Project: KZ acknowledges support from the National Young Scholar Award of the NSFC (#30125043), from the Basic Research Project (#2002CCA01500) of MOST, and from the Chung Kong Scholars Program administered by the Ministry of Education (PRC) and the Li Ka Shing Foundation (Hong Kong).

Intramolecular cyclization of N-alkoxyl amines are studied for the stereoselective preparation of 2, 4-disubstituted pyrrolidine derivatives. Reduction of oximes under acidic conditions by NaBH₃CN afforded the corresponding nucleophilic hydroxylamine derivatives, which subsequently cyclized via S_N2'mechanism to give the desired N-alkoxyl pyrrolidines.
- S_N'reaction,
- pyrrolidines,
- oxime,
- hydroxylamine
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