Synthesis of D-erythrose and D-threose derived nitrones and cycloadditions to styrene
1999
The new nitrones derived from cyclic acetals of D-erythrose
(2a-c) and D-threose (8) react with styrene to afford the
corresponding 3,5-disubstituted diastereomeric isoxazolidines
3-6 and 9-12. The stereoselectivity was dependent on the steric
hindrance of the nitrone. The major products 3a-c (55-58 %) and
9 (73 %) were found to have the C-3/C-4' erythro and C-3/C-5
cis relative configuration by X-ray analysis. Its formation can
be rationalized by less hindered endo attack of the Z-nitrone
in an antiperiplanar manner with respect to the largest group
of the cyclic acetal. (C) 1999 Elsevier Science Ltd. All rights
reserved.
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