Diastereoselective zinco-cyclopropanation of chiral allylic alcohols with gem-dizinc carbenoids.
The highly diastereoselective zinco-cyclopropanation of chiral allylic alcohols using gem-dizinc carbenoids is described. The reaction produces three contiguous stereogenic centers, and the resulting chiral cyclopropylzinc derivatives can be trapped with electrophiles with retention of configuration. Simple functional group manipulations lead to the efficient synthesis of orthogonally protected 1,2,3-substituted cyclopropane derivatives.
Fournier
Jean-François
JF
Département de Chimie, Université de Montréal, Montréal, Québec, Canada H3C 3J7.
Mathieu
Simon
S
Charette
André B
AB
D018360:Crystallography, X-Ray; D003500:Cyclization; D003521:Cyclopropanes / Q000138:chemical synthesis / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation; D009942:Organometallic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D020005:Propanols / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism; D015032:Zinc / Q000737:chemistry*
D003521:Cyclopropanes; D009942:Organometallic Compounds; D020005:Propanols; C006463:allyl alcohol; D015032:Zinc