Issue 12, 1994

Theoretical studies of nucleophilic additions of monomeric and dimeric organometallics

Abstract

The reaction pathways of nucleophilic addition of organometallic species to alkenes and carbonyl compounds have been studied by ab initio theoretical calculations. In the first part, the stereochemistry of the carbometallation of cyclopropene has been examined experimentally and theoretically for a model system to develop a rationale for the experimental stereoselectivity. In the second part, the reaction of a methyllithium dimer with aldehydes has been studied to obtain a basic understanding of the role of dimeric species in organic chemistry, especially, in asymmetric carbonyl additions. The principle of stereoselective carbonyl addition is compared with that of carbometallation of alkenes.

Article information

Article type
Paper

J. Chem. Soc., Faraday Trans., 1994,90, 1789-1798

Theoretical studies of nucleophilic additions of monomeric and dimeric organometallics

M. Nakamura, E. Nakamura, N. Koga and K. Morokuma, J. Chem. Soc., Faraday Trans., 1994, 90, 1789 DOI: 10.1039/FT9949001789

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