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Synthesis 2012; 44(12): 1898-1906
DOI: 10.1055/s-0031-1290973
DOI: 10.1055/s-0031-1290973
paper
Synthesis of α-Prolinols and 2-Amino-1,5-diols from Primary Nitroalkanes and Other Simple Precursors via Intermediacy of 5,6-Dihydro-4H-1,2-oxazines
Further Information
Publication History
Received: 10 February 2012
Accepted after revision: 20 March 2012
Publication Date:
25 May 2012 (online)
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Dedicated to Prof. Dr. H. Mayr on the occasion of his 65th birthday
Abstract
A new strategy for the synthesis of 2-(1-hydroxyalkyl)pyrrolidines and 2-amino-1,5-diols is suggested. The target compounds can be obtained in high yields from available precursors through the intermediacy of six-membered cyclic nitronates and their rearrangement products. Successive reduction of the latter led to the target products with moderate to high diastereoselectivity.
Key words
diastereoselective reduction - hydrogenation - 1,2-oxazine derivatives - amino alcohols - nitronesSupporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information