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Samarium‐Catalyzed Tandem Semipinacol Rearrangement/Tishchenko Reaction of α ‐Hydroxy Epoxides: A Novel Approach to Highly Stereoselective Construction of 2‐Quaternary 1,3‐Diol Units
Author(s) -
Fan ChunAn,
Wang BaoMin,
Tu YongQiang,
Song ZhenLei
Publication year - 2001
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(20011015)40:20<3877::aid-anie3877>3.0.co;2-s
Subject(s) - stereoselectivity , tandem , catalysis , diol , chemistry , samarium , combinatorial chemistry , stereochemistry , organic chemistry , materials science , composite material
Three contiguous stereocenters are constructed with high diastereoselectivity in a novel samarium‐catalyzed tandem reaction of α ‐hydroxy epoxides 1 to give exclusively the C1,C2‐ anti isomers of 2 and 2′ . This could lead to the development of a general procedure for the diastereoselective construction of 2‐quaternary 1,3‐diol units.