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Tandem Zn‐Brook Rearrangement/Ene‐Allene Carbocyclization
Author(s) -
Unger Rozalia,
Cohen Theodore,
Marek Ilan
Publication year - 2009
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200900043
Subject(s) - chemistry , allene , propargyl , diastereomer , tandem , ene reaction , stereochemistry , medicinal chemistry , catalysis , organic chemistry , materials science , composite material
The addition of metalated alkynes to acylsilanes leads to the corresponding α‐propargylsilanol derivatives. On addition of ZnBr 2 , Zn‐promoted Brook rearrangements take place to produce the propargyl/allenylzinc bromides, which undergo cyclization to give functionalized carbocycles as single diastereoisomers. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)