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Synfacts 2008(6): 0574-0574  
DOI: 10.1055/s-2008-1067073
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Acylaminopyrrolidines and -piperidines via Diastereoselective Ritter Reaction

Contributor(s): Victor Snieckus, Erhad Ascic
I. R. Morgan, A. Yazici, S. G. Pyne*, B. W. Skelton
University of Wollongong and University of Western Australia, Crawley, Australia
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Publication History

Publication Date:
21 May 2008 (online)

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Significance

Described is a two-step strategy for the synthesis of hydroxyl-acylaminopyrrolidines 5 and hydroxyl-acylaminopiperidines 6, employing a highly diastereoselective Ritter reaction of nitriles with in situ prepared chiral lactams 1 and 2, followed by acid hydrolysis of the resulting oxazoles 3 and 4 to yield the products 5 and 6 with high cis diastereoselectivity. Starting material 1 was prepared from the known (3S)-hydroxysuccinimide (P. Kocalka et al. Tetrahedron 2006, 62, 5763; P. Q. Huang Synlett 2006, 1133) while the hemiaminal (5S)-2 was prepared from N-PMB-(3S)-hydroxy­glutarimide (P. Q. Huang et al. Org. Lett. 2003, 5, 1927).