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Intermolecular Michael reactions: a computational investigation.

ABSTRACT: Computational studies have suggested that ?(3)-lithium enolates in which the cation is partially bound to both carbon and oxygen may be important reactive intermediates. DFT calculations are used to demonstrate that explicitly solvated acetone enolates are largely O-bound. With this premise in mind, the stereochemical course of intermolecular Michael additions is examined. The results are generally consistent with what is observed experimentally and the model advanced by Heathcock and co-workers.

SUBMITTER: Kwan EE

PROVIDER: S-EPMC2980588 | biostudies-other | 2010 Nov

REPOSITORIES: biostudies-other

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Intermolecular Michael reactions: a computational investigation.

Kwan Eugene E EE Evans David A DA

Organic letters 20101001 22

Computational studies have suggested that η(3)-lithium enolates in which the cation is partially bound to both carbon and oxygen may be important reactive intermediates. DFT calculations are used to demonstrate that explicitly solvated acetone enolates are largely O-bound. With this premise in mind, the stereochemical course of intermolecular Michael additions is examined. The results are generally consistent with what is observed experimentally and the model advanced by Heathcock and co-workers ...[more]

PMID: 20886873

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