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Diastereoselective Synthesis of Enantioenriched, Annulated Tetrahydrofurans by Simultaneous Formation of the O‐1C‐5 and the C‐5C‐4 Bonds
Author(s) -
Ünaldi Seda,
Özlügedik Mustafa,
Fröhlich Roland,
Hoppe Dieter
Publication year - 2005
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200505142
Subject(s) - stereocenter , chemistry , boron trifluoride , tetrahydrofuran , stereochemistry , boron , enantioselective synthesis , quaternary carbon , medicinal chemistry , carbon fibers , organic chemistry , catalysis , materials science , solvent , composite number , composite material
Enantiomerically enriched 1‐[2‐(1‐hydroxyalkyl)cycloalkylidene]methyl N , N ‐diisopropylcarbamates, which are easily available by an asymmetric homoaldol reaction, condense with aldehydes under the influence of boron trifluoride etherate to form cyclohexano‐ or cyclopentano‐annulated tetrahydrofuran‐3‐carboxaldehydes, bearing two quaternary carbon atoms and four adjacent stereogenic centers, with complete diastereoselectivity.