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Remarkable Stereocontrol in the Palladium‐Catalysed Cyclopropanation of Vinyl‐ and Dienylboronates by Substituted Diazoalkanes
Author(s) -
Markó István E,
Kumamoto Takuya,
Giard Thierry
Publication year - 2002
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/1615-4169(200212)344:10<1063::aid-adsc1063>3.0.co;2-l
Subject(s) - cyclopropanation , chemistry , palladium , catalysis , combinatorial chemistry , organic chemistry , medicinal chemistry , stereochemistry
Substituted diazoalkanes react smoothly, in the presence of catalytic amounts of Pd(OAc) 2 , with a range of vinyl‐ and dienylboronates, affording in good to excellent yields, the corresponding trisubstituted cyclopropanes. The reaction is remarkably regio‐, chemo‐, and diastereoselective. The synthetic utility of this novel protocol is illustrated by the efficient assembly of the middle fragment of ambruticin.