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Stereoselective Synthesis of Exocyclic Alkenes by Cu‐Catalyzed Allylmagnesiation, Pd‐Catalyzed Alkylation, and Ru‐Catalyzed Ring‐Closing Metathesis: Highly Stereoselective Synthesis of ( Z )‐ and ( E )‐γ‐Bisabolenes
Author(s) -
Anastasia Luigi,
Dumond Yves R.,
Negishi Eiichi
Publication year - 2001
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 - 10.1002/1099-0690(200108)2001:16<3039::aid-ejoc3039>3.0.co;2-v
Subject(s) - chemistry , stereoselectivity , ring closing metathesis , alkene , metathesis , alkylation , catalysis , stereochemistry , bromide , medicinal chemistry , organic chemistry , polymerization , polymer
Highly efficient stereoselective syntheses of both ( Z )‐ and ( E )‐γ‐bisabolenes ( 1 ) were achieved by ring closing metathesis of stereodefined tetrasubstituted alkenes. Both ( Z )‐ and ( E )‐tetrasubstituted alkene precursors were obtained by Cu‐catalyzed stereoselective addition of allylmagnesium bromide to propargyl alcohols, followed by Pd‐catalyzed cross coupling of alkylzinc derivatives. This represents the first application of ring‐closing metathesis to the stereoselective synthesis of exocyclic alkenes.