Abstract
AbstractThe addition of reagents to trigonal carbon to give tetrahedral centers and its reverse involve the stereogenetic aspect known as face selection, which has ramifications throughout organic chemistry. Some of the root factors of face selection (e.g., steric and conformational) have long been understood in principle, but the electronic contribution of substituents and skeletal changes is controversial. The principal models for the electronic basis of face selection are those of Felkin, Anh and Cieplak. It is argued that none of the three are either right or wrong, but that the contribution each can make, varies from case to case. Each of them may become dominant depending on the reaction at issue.
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