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Diastereoselective synthesis of (2R,4S,5S)-(+)-5-(2,2-dichloroacetamido)- 4-(4-nitrophenyl)-2-aryl-1,3-dioxanes

✍ Scribed by Liu Jun; Li Jun; Yang Shaorong; Li Hua; Hu Quanyuan; Xu Hansheng; Hu Xianming

Publisher
Journal of Heterocyclic Chemistry
Year
2001
Tongue
English
Weight
50 KB
Volume
38
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

(2__R__,4__S__,5__S__)‐(+)‐5‐(2,2‐Dichloroacetamido)‐4‐(4‐nitrophenyl)‐2‐aryl‐1,3‐dioxanes 3–8 were synthesized with high diastereoselectivity and good yields. The structures of acetals were determined and the configurations were confirmed by 2D‐NMR (NOESY) and X‐ray crystallographic analysis.

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An improved synthesis of (4S,5S)-2,2-dim
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The condensation of (1 R,2S) or (lS,2S)-N,N'-dimethyI-l-phenylpropane-l 2-diamines with aldehydes gives respectively two diastereorneric 2-alkyl-l,3,4-trimethyI-S-phen limidazolidines. At thermodynamical equilibrium the major isomer in the erythro series is this one where t f ! e substituents at pos