One Flask Synthesis of t-2, c-3-Disubstituted 5-Oxo-r-1-cyclopentanecarboxamides by a SmI_2/HMPA-Induced Stereoselective Reductive Coupling/Dieckmann Condensation Sequence of α,β-Unsaturated Amides
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- Yamamoto Hidetoshi
- Institute of Advanced Material Study, Kyushu University
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- Kobayashi Shigeru
- Institute of Advanced Material Study, Kyushu University
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- Kanemasa Shuji
- Institute of Advanced Material Study, Kyushu University
Bibliographic Information
- Other Title
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- One Flask Synthesis of t 2 c 3 Disubsti
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Abstract
α,β-Unsaturated amides undergo highly dl-selective reductive coupling reactions by the action of SmI_2-HMPA. Subsequent Dieckmann condensation is followed in the same flask when the amides bear small N-substituents: N, N-dibenzylamides afford 3, 4-disubstituted dl-adipamides as reductive coupling products; N, N-dimethylamides give t-2, c-3-disubstituted 5-oxo-γ-1-cyclopentanecarboxamides as Dieckmann condensation products, both in exclusively dl-selective manners.
Journal
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- 九州大学機能物質科学研究所報告
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九州大学機能物質科学研究所報告 9 (1), 21-26, 1995-11-15
Institute of Advanced Material Study Kyushu University
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Details 詳細情報について
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- CRID
- 1390572174788978048
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- NII Article ID
- 110006177460
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- NII Book ID
- AN10060378
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- ISSN
- 09143793
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- DOI
- 10.15017/6668
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- HANDLE
- 2324/6668
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- NDL BIB ID
- 3915745
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- Text Lang
- en
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- Data Source
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- JaLC
- IRDB
- NDL
- CiNii Articles
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- Abstract License Flag
- Allowed