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Nickel-catalyzed enantioselective allylic alkylation of lactones and lactams with unactivated allylic alcohols.

ABSTRACT: The first nickel-catalyzed enantioselective allylic alkylation of lactone and lactam substrates to deliver products bearing an all-carbon quaternary stereocenter is reported. The reaction, which utilizes a commercially available chiral bisphosphine ligand, proceeds in good yield with a high level of enantioselectivity (up to 90% ee) on a range of unactivated allylic alcohols for both lactone and lactam nucleophiles. The utility of this method is further highlighted via a number of synthetically useful product transformations.

SUBMITTER: Ngamnithiporn A 

PROVIDER: S-EPMC5912103 | biostudies-other | 2018 Mar

REPOSITORIES: biostudies-other

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Nickel-catalyzed enantioselective allylic alkylation of lactones and lactams with unactivated allylic alcohols.

Ngamnithiporn Aurapat A   Jette Carina I CI   Bachman Shoshana S   Virgil Scott C SC   Stoltz Brian M BM  

Chemical science 20180124 9

The first nickel-catalyzed enantioselective allylic alkylation of lactone and lactam substrates to deliver products bearing an all-carbon quaternary stereocenter is reported. The reaction, which utilizes a commercially available chiral bisphosphine ligand, proceeds in good yield with a high level of enantioselectivity (up to 90% ee) on a range of unactivated allylic alcohols for both lactone and lactam nucleophiles. The utility of this method is further highlighted <i>via</i> a number of synthet  ...[more]