Ontology highlight
ABSTRACT:
SUBMITTER: Schmitt DC
PROVIDER: S-EPMC3321131 | biostudies-literature | 2012 Apr
REPOSITORIES: biostudies-literature
The Journal of organic chemistry 20120315 7
Silyl glyoxylates react with enolates and enones to afford either glycolate aldol or Michael adducts. Product identity is controlled by the countercation associated with the enolate. Reformatsky nucleophiles in the presence of additional Zn(OTf)(2) result in aldol coupling (A), while lithium enolates provide the Michael coupling (B). Deprotonation of the aldol product A with LDA induces equilibration to form the minor diastereomer of Michael product B. This observation suggests that formation of ...[more]