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Direct Catalytic Asymmetric Mannich Reactions for the Construction of Quaternary Carbon Stereocenters.

ABSTRACT: Herein, we report a Zn-ProPhenol catalyzed Mannich reaction using ?-branched ketones as nucleophilic partners for the direct enantio- and diastereoselective construction of quaternary carbon stereocenters. The reaction can be run on a gram-scale with a low catalyst loading without impacting its efficiency. Moreover, the Mannich adducts can be further elaborated with complete diastereocontrol to access molecules possessing complex stereotriads.

SUBMITTER: Trost BM 

PROVIDER: S-EPMC4866641 | biostudies-literature | 2016 Mar

REPOSITORIES: biostudies-literature

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Direct Catalytic Asymmetric Mannich Reactions for the Construction of Quaternary Carbon Stereocenters.

Trost Barry M BM   Saget Tanguy T   Hung Chao-I Joey CI  

Journal of the American Chemical Society 20160309 11

Herein, we report a Zn-ProPhenol catalyzed Mannich reaction using α-branched ketones as nucleophilic partners for the direct enantio- and diastereoselective construction of quaternary carbon stereocenters. The reaction can be run on a gram-scale with a low catalyst loading without impacting its efficiency. Moreover, the Mannich adducts can be further elaborated with complete diastereocontrol to access molecules possessing complex stereotriads. ...[more]

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