4-benzyl-2,3-didehydroprolinate as a homochiral template for michael additions. Synthesis of enantiopure α-allokainoids, β-kainoids, 2,3-methanoprolines and other 3,4-disubstituted prolines

Ethyl (4 R)- N-methoxycarbonyl-4-benzyl-2,3-didehydroprolinate 10a undergoes Michael additions with stabilized carbanions and cuprates giving exclusively the enantiopure all- trans 3,4-disubstituted prolinates. The high stereoselection observed in this reaction is driven by the C-4 substituent of th...

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Published in:Tetrahedron: asymmetry 1996-09, Vol.7 (9), p.2613-2626
Main Authors: Ezquerra, Jesús, Escribano, Ana, Rubio, Almudena, Remuiñán, Modesto Jesús, Vaquero, Juan José
Format: Article
Language:English
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Summary:Ethyl (4 R)- N-methoxycarbonyl-4-benzyl-2,3-didehydroprolinate 10a undergoes Michael additions with stabilized carbanions and cuprates giving exclusively the enantiopure all- trans 3,4-disubstituted prolinates. The high stereoselection observed in this reaction is driven by the C-4 substituent of the Michael acceptor. This methodology has been applied to the synthesis of the enantiopure β-kainoid 5a and the 2,3-methanoproline 15. Ethyl (4R) N-urethane-4-benzyl-2,3-didehydroprolinate 10 undergoes Michael addition with stabilized carbanions and cuprates giving exclusively the enantiopure all- trans 3,4-disubstituted prolinates 11.
ISSN:0957-4166
1362-511X
DOI:10.1016/0957-4166(96)00336-9