Alkenes as Chelating Groups in Diastereoselective Additions of Organometallics to Ketones.

abstract

• Alkenes have been discovered to be chelating groups to Zn(II), enforcing highly stereoselective additions of organozincs to ,-unsaturated ketones. 1H NMR studies and DFT calculations provide support for this surprising chelation mode. The results expand the range of coordinating groups for chelation-controlled carbonyl additions from heteroatom Lewis bases to simple C-C double bonds, broadening the 60 year old paradigm.

authors

• Gutierrez Santacruz, Osvaldo

published proceedings

• Organometallics

altmetric score

• 0.25

author list (cited authors)

• Raffier, L., Gutierrez, O., Stanton, G. R., Kozlowski, M. C., & Walsh, P. J.

citation count

• 3

complete list of authors

• Raffier, Ludovic||Gutierrez, Osvaldo||Stanton, Gretchen R||Kozlowski, Marisa C||Walsh, Patrick J

publication date

• January 2014

publisher

• American Chemical Society (ACS)  Publisher

published in

• Organometallics  Journal

PubMed Central ID

• 25328269

Digital Object Identifier (DOI)

• 10.1021/om5007006

start page

• 5371

end page

• 5377

volume

• 33

issue

• 19

URL

• http://dx.doi.org/10.1021/om5007006