A thermodynamic preference of chiral N-methanesulfonyl and N-arenesulfonyl 2,3-cis-3-alkyl-2-vinylaziridines over their 2,3-trans-isomers: Useful palladium(0)-catalyzed equilibration reactions for the synthesis of (E)-alkene dipeptide isosteres

被引：111

作者：

Ibuka, T ^{[1
]}

Mimura, N ^{[1
]}

Aoyama, H ^{[1
]}

Akaji, M ^{[1
]}

Ohno, H ^{[1
]}

Miwa, Y ^{[1
]}

Taga, T ^{[1
]}

Nakai, K ^{[1
]}

Tamamura, H ^{[1
]}

Fujii, N ^{[1
]}

Yamamoto, Y ^{[1
]}

机构：

[1] TOHOKU UNIV,DEPT CHEM,GRAD SCH SCI,SENDAI,MIYAGI 980,JAPAN

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1997年 / 62卷 / 04期

关键词：

D O I：

10.1021/jo961760o

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Palladium(0)-catalyzed reactions of N-methanesulfonyl- or N-(arenesulfonyl)-3-alkyl-2-vinylaziridines reveal that 2,3-cis-isomers are more stable than the corresponding 2,3-trans-isomers in accord with ab initio calculations. A highly stereoselective synthetic route to (E)-alkene dipeptide isosteres having desired stereochemistries from 2,3-cis-3-isobutyl-2-vinylaziridine by the use of organocopper chemistry is also presented.

引用

页码：999 / 1015

页数：17

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