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Small but Effective: Copper Hydride Catalyzed Synthesis of α‐Hydroxyallenes
Author(s) -
Deutsch Carl,
Lipshutz Bruce H.,
Krause Norbert
Publication year - 2007
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/anie.200603739
Subject(s) - propargyl , chemistry , cycloisomerization , hydride , catalysis , copper , sn2 reaction , carbene , ligand (biochemistry) , combinatorial chemistry , medicinal chemistry , organic chemistry , metal , receptor , biochemistry
Mild and efficient : The copper hydride catalyzed diastereoselective S N 2′ reduction of propargyl oxiranes provides α‐hydroxyallenes bearing various functional groups (ethers, esters, alcohols; see scheme, PMHS=polymethylhydridosiloxane). The best results were obtained with a copper hydride catalyst and an N‐heterocyclic carbene ligand. The resulting allenes are useful substrates, as they undergo, for example, regio‐ and chemoselective cycloisomerization to give 2,5‐dihydrofurans.