An Asymmetric Ugi Three-Component Reaction Induced by Chiral Cyclic Imines: Synthesis of Morpholin– or Piperazine–Keto-carboxamide Derivatives
A series of chiral 5,6-dihydro-1,4-oxazin-2-one substrates, as preformed cyclic aldimines and ketoimines, were employed to develop a new asymmetric Ugi three-component reaction for the first time. The Ugi reaction of the imines, isocyanides, and carboxylic acids opens an efficient access to novel mo...
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| Veröffentlicht in: | Journal of organic chemistry 2012-02, Vol.77 (3), p.1386-1395 |
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| container_end_page | 1395 |
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| container_issue | 3 |
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| container_title | Journal of organic chemistry |
| container_volume | 77 |
| creator | Zhu, Deguang Xia, Liang Pan, Li Li, Sheng Chen, Ruijiao Mou, Yongren Chen, Xiaochuan |
| description | A series of chiral 5,6-dihydro-1,4-oxazin-2-one substrates, as preformed cyclic aldimines and ketoimines, were employed to develop a new asymmetric Ugi three-component reaction for the first time. The Ugi reaction of the imines, isocyanides, and carboxylic acids opens an efficient access to novel morpholin-2-one-3-carboxamide compounds. The chiral imines showed promising stereoinduction for the new chiral center of the Ugi products, and predominant trans-isomers were obtained in the most cases. Addition of some Lewis acids or proton acids could improve the diastereoselectivity further but usually led to a drop in total yield. The Ugi-3CR could be extended to the stereoselective synthesis of ketopiperazine-2-carboxamide derivatives. |
| doi_str_mv | 10.1021/jo2021967 |
| format | Article |
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Org. Chem</addtitle><description>A series of chiral 5,6-dihydro-1,4-oxazin-2-one substrates, as preformed cyclic aldimines and ketoimines, were employed to develop a new asymmetric Ugi three-component reaction for the first time. The Ugi reaction of the imines, isocyanides, and carboxylic acids opens an efficient access to novel morpholin-2-one-3-carboxamide compounds. The chiral imines showed promising stereoinduction for the new chiral center of the Ugi products, and predominant trans-isomers were obtained in the most cases. Addition of some Lewis acids or proton acids could improve the diastereoselectivity further but usually led to a drop in total yield. 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Org. Chem</addtitle><date>2012-02-03</date><risdate>2012</risdate><volume>77</volume><issue>3</issue><spage>1386</spage><epage>1395</epage><pages>1386-1395</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>A series of chiral 5,6-dihydro-1,4-oxazin-2-one substrates, as preformed cyclic aldimines and ketoimines, were employed to develop a new asymmetric Ugi three-component reaction for the first time. The Ugi reaction of the imines, isocyanides, and carboxylic acids opens an efficient access to novel morpholin-2-one-3-carboxamide compounds. The chiral imines showed promising stereoinduction for the new chiral center of the Ugi products, and predominant trans-isomers were obtained in the most cases. Addition of some Lewis acids or proton acids could improve the diastereoselectivity further but usually led to a drop in total yield. The Ugi-3CR could be extended to the stereoselective synthesis of ketopiperazine-2-carboxamide derivatives.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>22224946</pmid><doi>10.1021/jo2021967</doi><tpages>10</tpages></addata></record> |
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| ispartof | Journal of organic chemistry, 2012-02, Vol.77 (3), p.1386-1395 |
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| language | eng |
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| source | American Chemical Society Journals |
| subjects | Chemistry Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings Organic chemistry Preparations and properties |
| title | An Asymmetric Ugi Three-Component Reaction Induced by Chiral Cyclic Imines: Synthesis of Morpholin– or Piperazine–Keto-carboxamide Derivatives |
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