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Enantioselective synthesis of dialkylated N-heterocycles by palladium-catalyzed allylic alkylation.

ABSTRACT: The enantioselective synthesis of ?-disubstituted N-heterocyclic carbonyl compounds has been accomplished using palladium-catalyzed allylic alkylation. These catalytic conditions enable access to various heterocycles, such as morpholinone, thiomorpholinone, oxazolidin-4-one, 1,2-oxazepan-3-one, 1,3-oxazinan-4-one, and structurally related lactams, all bearing fully substituted ?-positions. Broad functional group tolerance was explored at the ?-position in the morpholinone series. We demonstrate the utility of this method by performing various transformations on our useful products to readily access a number of enantioenriched compounds.

SUBMITTER: Numajiri Y 

PROVIDER: S-EPMC6410707 | biostudies-literature | 2015 Mar

REPOSITORIES: biostudies-literature

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Enantioselective synthesis of dialkylated N-heterocycles by palladium-catalyzed allylic alkylation.

Numajiri Yoshitaka Y   Jiménez-Osés Gonzalo G   Wang Bo B   Houk K N KN   Stoltz Brian M BM  

Organic letters 20150225 5

The enantioselective synthesis of α-disubstituted N-heterocyclic carbonyl compounds has been accomplished using palladium-catalyzed allylic alkylation. These catalytic conditions enable access to various heterocycles, such as morpholinone, thiomorpholinone, oxazolidin-4-one, 1,2-oxazepan-3-one, 1,3-oxazinan-4-one, and structurally related lactams, all bearing fully substituted α-positions. Broad functional group tolerance was explored at the α-position in the morpholinone series. We demonstrate  ...[more]

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