STEREOCONTROL IN INTERMOLECULAR NUCLEOPHILIC ADDITION TO N-ACYLIMINIUM ION DIRECTED BY A BICYCLO[2.2.1]HEPTENE OR 7-OXABICYCLO[2.2.1]HEPTENE GROUP. A NOVEL ROUTE TO 5-SUBSTITUTED 3-PYRROLIN-2-ONES OF HIGH OPTICAL PURITY
STEREOCONTROL IN INTERMOLECULAR NUCLEOPHILIC ADDITION TO N-ACYLIMINIUM ION DIRECTED BY A BICYCLO[2.2.1]HEPTENE OR 7-OXABICYCLO[2.2.1]HEPTENE GROUP. A NOVEL ROUTE TO 5-SUBSTITUTED 3-PYRROLIN-2-ONES OF HIGH OPTICAL PURITY
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DOI：
10.1248/cpb.40.1670
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发表时间：
1992-06
影响因子：
1.7
通讯作者：
Y. Arai;A. Fujii;Toshiyuki Ohno;T. Koizumi
中科院分区：
文献类型：
--
作者：
Y. Arai;A. Fujii;Toshiyuki Ohno;T. Koizumi
分子间的亲核加成的构象刚性，三环吡咯烷离子（来自2或6）发生专门从较少的阻碍面与其双环[2.2.1]庚烯或7-氧杂双环[2.2.1]庚烯部分融合。所得手性7-氧杂双环[2.2.1]庚烯体系的逆Diels-桤木断裂提供了5-取代的3-吡咯啉-2-酮，而不损失光学纯度。
Intermolecular nucleophilic additions to the conformationally rigid, tricyclic pyrrolidinium ion (derived from 2 or 6) took place exclusively from the less-hindered face fused with its bicyclo[2.2.1]heptene or 7-oxabicyclo[2.2.1]heptene moiety. Retro-Diels-Alder fragmentation of the resulting chiral 7-oxabicyclo[2.2.1]heptene system furnished a 5-substituted 3-pyrrolin-2-one without a loss of optical purity.