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Palladium-Catalyzed Enantioselective C_sp³-C_sp³ Cross-Coupling for the Synthesis of (Poly)fluorinated Chiral Building Blocks.

ABSTRACT: A general method for the enantioselective synthesis of carbo- and heterocyclic carbonyl compounds bearing fluorinated α-tetrasubstituted stereocenters using palladium-catalyzed decarboxylative allylic alkylation is described. The stereoselective C_sp³-C_sp³ cross-coupling reaction delivers five- and six-membered ketone and lactam products bearing (poly)fluorinated tetrasubstituted chiral centers in high yields and enantioselectivities. These fluorinated, stereochemically rich building blocks hold potential value in medicinal chemistry and are prepared using an orthogonal and enantioselective approach into such chiral moieties compared to traditional approaches, often without the use of electrophilic fluorinating reagents.

SUBMITTER: Lu Y

PROVIDER: S-EPMC6192028 | biostudies-literature | 2018 Sep

REPOSITORIES: biostudies-literature

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Palladium-Catalyzed Enantioselective Csp3-Csp3 Cross-Coupling for the Synthesis of (Poly)fluorinated Chiral Building Blocks.

Lu Yanhui Y Goldstein Elizabeth L EL Stoltz Brian M BM

Organic letters 20180905 18

A general method for the enantioselective synthesis of carbo- and heterocyclic carbonyl compounds bearing fluorinated α-tetrasubstituted stereocenters using palladium-catalyzed decarboxylative allylic alkylation is described. The stereoselective Csp3-Csp3 cross-coupling reaction delivers five- and six-membered ketone and lactam products bearing (poly)fluorinated tetrasubstituted chiral centers in high yields and enantioselectivities. These fluorinated, ...[more]

PMID: 30183315

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