Synthesis 2012; 44(12): 1898-1906
DOI: 10.1055/s-0031-1290973
paper
© Georg Thieme Verlag Stuttgart · New York

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

Andrey A. Tabolin*
N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky prosp. 47, Moscow 119991, Russian Federation, Fax: +7(499)1355328   Email: iof@ioc.ac.ru
,
Alexey V. Lesiv
N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky prosp. 47, Moscow 119991, Russian Federation, Fax: +7(499)1355328   Email: iof@ioc.ac.ru
,
Yulia A. Khomutova
N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky prosp. 47, Moscow 119991, Russian Federation, Fax: +7(499)1355328   Email: iof@ioc.ac.ru
,
Sema L. Ioffe*
N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky prosp. 47, Moscow 119991, Russian Federation, Fax: +7(499)1355328   Email: iof@ioc.ac.ru
› Author Affiliations
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.

Supporting Information