2010年12月
Studies on two different diastereoselective reaction pathways from a serinol derivative to 4-hydroxymethyl-2-oxazolidinones using 2-chloroethyl chloroformate and N,N '-disuccinimidyl carbonate
TETRAHEDRON-ASYMMETRY
- ,
- 巻
- 21
- 号
- 24
- 開始ページ
- 2904
- 終了ページ
- 2910
- 記述言語
- 英語
- 掲載種別
- DOI
- 10.1016/j.tetasy.2010.11.022
- 出版者・発行元
- PERGAMON-ELSEVIER SCIENCE LTD
Two reaction pathways and their diastereoselectivity-determining steps of the asymmetric desymmetrization of (R)-2-(alpha-methylbenzyl)amino-1,3-propanediol 1 with 2-chloroethyl chloroformate (CCF) and with N,N'-disuccinimidyl carbonate giving (4S,alpha R)-4-hydroxymethyl-3-alpha-methylbenzyl-2-oxazolidinones (4S)-3 and its (4R,alpha R)-diastereomer (4R)-3 were investigated. The reaction of serinol 1 and CCF to give the corresponding carbonates was not a diastereoselectivity-determining step. The carbonates gave (R)-5-(alpha-methylbenzyl)amino-1,3-dioxan-2-one 4 after addition of DBU, and an intramolecular acyl transfer of 4 was found to be a diastereoselectivity-determining step to give (4S)-3. Conversely, the reaction of serinol 1 and N,N'-disuccinimidyl carbonate afforded directly the opposite diastereomer (4R)-3 but not via the intermediate 4. Thus, their diastereoselectivities depended on the acylating reagent. (C) 2010 Elsevier Ltd. All rights reserved.
- リンク情報
- ID情報
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- DOI : 10.1016/j.tetasy.2010.11.022
- ISSN : 0957-4166
- CiNii Articles ID : 80021638690
- Web of Science ID : WOS:000287295400003