Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 21, Issue 12, Pages 4551-4555Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201500176
Keywords
allylation; asymmetric catalysis; rearrangement; stereoselectivity; total synthesis
Categories
Funding
- Leverhulme Trust [F00 261AD]
- LU
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A new, highly efficient Lewis base catalyst for a practical enantio- and diastereoselective crotylation of unsaturated aldehydes with E- and Z-crotyltrichlorosilanes has been developed. The method was employed as a key step in a novel asymmetric synthesis of bioactive serrulatane diterpene (-)-elisabethadione. Other strategic reactions for setting up the stereogenic centers included anionic oxy-Cope rearrangement and cationic cyclization. The synthetic route relies on simple, high yielding reactions and avoids use of protecting groups or chiral auxiliaries.
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