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Synthesis 2003(9): 1329-1334
DOI: 10.1055/s-2003-40201
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

1,3-Dipolar Cycloaddition Reactions of Nitrones to Prop-1-ene-1,3-sultone

Li Tian, Guo-Yan Xu, Yong Ye, Lun-Zu Liu*
State Key Laboratory of Elemento-Organic Chemistry, Institute of Elemento-Organic Chemistry, Nankai University, Tianjin, 300071, P. R. China
e-Mail: tian_lili@eyou.com;
Further Information

Publication History

Received 17 February 2003
Publication Date:
24 June 2003 (online)

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Abstract

The reaction of prop-1-ene-1,3-sultone (1) with a variety of nitrones 2 afforded novel [3+2] cycloaddition products 3, 4, and 5 in good yield. Excellent regio- and stereoselectivity were achieved in the cycloaddition reaction with phenylnitrones.

Key words

cycloaddition - nitrone - sultone - regioselectivity - stereoselectivity­

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8

The various substituted phenylnitrones 2a-l have been widely employed as 1,3-dipoles. Three methods have been reported for their preparation. [9-11] Two routes (Method A and Method B) have been used by us (Scheme [2] ). Method A has two steps. In the first step, nitrobenzene was reduced by zinc dust and NH4Cl to phenylhydroxylamine by a modified literature procedure, [12] and was purified by recrystallization. In the second step, the purified hydroxylamine was mixed with an equimolar amount of benzaldehyde to give the corresponding nitrones. Method B can be used to synthesize nitrones whose phenylhydroxylamines were unstable and can not be separated as pure intermediates. In Method B, the two steps used in Method A occur successively in one-pot. Cyclic nitrones 2m and 2n were prepared according to the reported procedures (Method C). [7]

19

Among numerous synthetic methods, [1] [20] [21] two routes attracted our attention. We repeated and improved the two methods [Method D (Scheme [3] ) and Method E (Scheme [4] )].