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
Rok vydání:	2006
Předmět:	Chemistry Stereochemistry Organic Chemistry Enantioselective synthesis Protonation General Chemistry Stereocenter Electrophilic substitution chemistry.chemical_compound Furan Michael reaction Physical and Theoretical Chemistry Enantiomer Butenolide
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
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::3afd2d7b0ccdd528f53cdc63fc228c13 https://doi.org/10.1002/jlac.199619960904 Zobrazit plný text záznamu Plný text