1998年7月
Reactions of a beta-sultam ring with Lewis acids via the C-S bond cleavage
TETRAHEDRON
- ,
- ,
- ,
- ,
- 巻
- 54
- 号
- 31
- 開始ページ
- 8941
- 終了ページ
- 8974
- 記述言語
- 英語
- 掲載種別
- DOI
- 10.1016/S0040-4020(98)00510-9
- 出版者・発行元
- PERGAMON-ELSEVIER SCIENCE LTD
Selective C-S bond cleavage of a beta-sultam ring was achieved by the reactions with Lewis acids. Aryl ketones or aldehyde were provided from 3-aryl-beta-sultams whereas beta-sultams bearing a poorly migratory substituent at C-3 gave trans-1,2,3-oxathiazolidine 2-oxides and/or cis-aziridines. These reactions were influenced by the cation-stabilizing capability of C-4 substituents and by the configuration of the substituents at C-3 and C-4. Some 4-alkenyl-3-aryl-beta-sultams underwent tandem intramolecular cyclization to give bicyclo[3.2.1]- and [2.2.1]-gamma-sultams via the processes of C-S bond cleavage, 1,2-aryl shift, cation-olefin cyclization and recombination of the sulfonyl anion. (C) 1998 Elsevier Science Ltd. All rights reserved.
- リンク情報
- ID情報
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- DOI : 10.1016/S0040-4020(98)00510-9
- ISSN : 0040-4020
- CiNii Articles ID : 80010440037
- Web of Science ID : WOS:000074744700004