2016
DOI: 10.1002/ange.201509983
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Carbocyclic Amino Ketones by Bredt's Rule‐Arrested Kulinkovich–de Meijere Reaction

Abstract: The Ti II -mediated formation of cyclopropylamines from alkenes and amides,the Kulinkovich-de Meijere reaction, involves two carbon-carbon bond-forming steps.Strategic use of at ricyclic intermediate can arrest the process if the second step requires formation of ab ridgehead double bond. Use of this Bredts rule constraint results in the production of carbocyclic amino ketones,key alkaloid building blocks.

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“…A recent modification of the Kulinkovich-de Meijere reaction allows for the synthesis of carbocyclic amino ketones mediated by Ti(O i Pr) 4 /RMgBr (REF 104 ) (FIG. 3b, top).…”
Section: Reductive Coupling Reactionsmentioning
confidence: 99%
“…A recent modification of the Kulinkovich-de Meijere reaction allows for the synthesis of carbocyclic amino ketones mediated by Ti(O i Pr) 4 /RMgBr (REF 104 ) (FIG. 3b, top).…”
Section: Reductive Coupling Reactionsmentioning
confidence: 99%