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Catalytic Enantioselective Allylic Amination of Olefins for the Synthesis of ent-Sitagliptin.

ABSTRACT: The presence of nitrogen atoms in most chiral pharmaceutical drugs has motivated the development of numerous strategies for the synthesis of enantioenriched amines. Current methods are based on the multi-step transformation of pre-functionalized allylic electrophiles into chiral allylic amines. The enantioselective allylic amination of unactivated olefins represents a more direct and attractive strategy. We report the enantioselective synthesis of ent-sitagliptin via an allylic amination of an unactivated terminal olefin.

SUBMITTER: Bao H

PROVIDER: S-EPMC4219538 | biostudies-literature | 2013 Nov

REPOSITORIES: biostudies-literature

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Catalytic Enantioselective Allylic Amination of Olefins for the Synthesis of <i>ent</i>-Sitagliptin.

Bao Hongli H Bayeh Liela L Tambar Uttam K UK

Synlett : accounts and rapid communications in synthetic organic chemistry 20131101 18

The presence of nitrogen atoms in most chiral pharmaceutical drugs has motivated the development of numerous strategies for the synthesis of enantioenriched amines. Current methods are based on the multi-step transformation of pre-functionalized allylic electrophiles into chiral allylic amines. The enantioselective allylic amination of unactivated olefins represents a more direct and attractive strategy. We report the enantioselective synthesis of <i>ent</i>-sitagliptin via an allylic amination ...[more]

PMID: 25378809

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