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Stereoselective Synthesis and Palladium‐Catalyzed Transformations of 2‐Alkylidene‐ 5‐vinyltetrahydrofurans
Author(s) -
Langer Peter,
Holtz Edith
Publication year - 2000
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/1521-3773(20000901)39:17<3086::aid-anie3086>3.0.co;2-f
Subject(s) - stereoselectivity , stereocenter , chemistry , palladium , catalysis , domino , lithium diisopropylamide , cascade reaction , sulfoxide , lithium (medication) , medicinal chemistry , combinatorial chemistry , organic chemistry , stereochemistry , enantioselective synthesis , deprotonation , ion , medicine , endocrinology
Up to three stereocenters are selectively formed in the new domino C,O‐cyclodialkylation of dilithiated 1,3‐dicarbonyl compounds with 1,4‐dibromo‐2‐butene. This reaction opens an efficient regio‐ and stereoselective route to a large range of 2‐alkylidene‐5‐vinyltetrahydrofurans (one example shown in scheme). These products were transformed in a new Pd‐catalyzed rearrangement reaction into functionalized bicyclo[3.2.1]octan‐8‐ones, whose skeleton is present in a large number of pharmacologically important natural products. LDA=lithium diisopropylamide, dppe=1,2‐bis(diphenylphosphanyl)ethane, DMSO=dimethyl sulfoxide.