Diastereo- and Enantioselective Synthesis of Lignan Building Blocks by Tandem Michael Addition/Electrophilic Substitution of Lithiated α-Amino Nitriles to Furan-2(5H)-one
Autor: | Jochen Kirchhoff, Vivien Lausberg, Dieter Enders |
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Rok vydání: | 2006 |
Předmět: | |
Zdroj: | Liebigs Annalen. 1996:1361-1366 |
ISSN: | 1099-0690 0947-3440 |
Popis: | Starting from chiral α-amino nitriles (S,S,R/S)-3, we prepared β-aroyl-γ-butyrolactones (S)-5 as well as 2,3-disubstituted γ -butyrolactones (S,S)- or (R,S,R)-6 in high yields and with high enantiomeric excesses by conjugate addition to butenolide, followed by protonation, α-alkylation or α-aldol addition, respectively. The introduction of one up to three stereogenic centers opens a flexible and highly efficient diastereo- and enantioselective route to 2,3-dibenzylated γ-butyrolactones 6, which proved to be important lignan building blocks. |
Databáze: | OpenAIRE |
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