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ZnBr 2 ‐Catalyzed Insertions of Carbonyl Compounds into Silacyclopropanes: Regiochemical Reversal Dependent on Metal Salt
Author(s) -
Franz Annaliese K.,
Woerpel K. A.
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(20001201)39:23<4295::aid-anie4295>3.0.co;2-a
Subject(s) - regioselectivity , structural isomer , catalysis , chemistry , salt (chemistry) , metal , zinc , combinatorial chemistry , organic chemistry , medicinal chemistry
Surprising catalyst‐based regiocontrol : Copper or zinc salts can be employed for the insertion of various carbonyl compounds into silacyclopropanes to afford, respectively, the 1,2‐ and 1,3‐regioisomers of the product with >99:1 regioselectivity (see scheme). Catalysis by ZnBr 2 allows access to previously unobserved products. The effects of additives such as H 2 O, menthol, and di‐ tert ‐butylpyridine on the regioselectivity of this insertion process are described.