Enantioselective synthesis of 1,2,3-trisubstituted cyclopropanes using gem-dizinc reagents.
The first asymmetric cyclopropanation of allylic alcohols using gem-dizinc carbenoids, which allows the synthesis of 1,2,3-substituted cyclopropane derivatives in high yields and excellent enantio- and diastereoselectivities, is reported. The initially formed cyclopropylzinc undergoes an in situ B/Zn exchange with the stoichiometric chiral ligand to generate a cyclopropyl borinate that can be directly engaged in a Suzuki-Miyaura cross-coupling reaction.
Zimmer
Lucie E
LE
Dpartement de Chimie, Université de Montréal, P.O. Box 6138, Station Downtown, Montréal, Québec, Canada H3C 3J7.
Charette
André B
AB
D003521:Cyclopropanes / Q000138:chemical synthesis* / Q000737:chemistry; D007202:Indicators and Reagents / Q000737:chemistry*; D013237:Stereoisomerism; D015032:Zinc / Q000737:chemistry*
D003521:Cyclopropanes; D007202:Indicators and Reagents; C030797:cyclopropane; D015032:Zinc