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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 22, 1992 - Issue 20
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Original Articles

Synthesis of Enantiopure N-tert-Butoxycarbonyl-2-aminocycloalkanones

Jeffrey Aubé Departments of Medicinal Chemistry and Chemistry, University of Kansas Lawrence, Kansas, 66045-2506
,
Michael S. Wolfe Departments of Medicinal Chemistry and Chemistry, University of Kansas Lawrence, Kansas, 66045-2506
,
Rhonda K. Yantiss Departments of Medicinal Chemistry and Chemistry, University of Kansas Lawrence, Kansas, 66045-2506
,
Scott M. Cook Departments of Medicinal Chemistry and Chemistry, University of Kansas Lawrence, Kansas, 66045-2506
&
Fusao Takusagawa Departments of Medicinal Chemistry and Chemistry, University of Kansas Lawrence, Kansas, 66045-2506; X-ray crystallographic facility, Department of Chemistry
Pages 3003-3012 | Received 09 Jun 1992, Published online: 23 Sep 2006
 
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Abstract

A route to enantiomerically pure N-tert-butoxycarbonyl-2-aminocycloalkanones (ring size: 5-8 membered) from the corresponding cycloalkene oxides is described. The procedure involves (1) aminolysis with (S)-α-methylbenzylamine/Me3A1 and chromatographic separation of diastereomers, (2) hydrogenolysis to afford the trans-2-aminocycloalkanols, (3) tert-butoxycarbonyl (Boc) protection, and (4) PCC oxidation.

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