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Regiodivergent enantioselective C-H functionalization of Boc-1,3-oxazinanes for the synthesis of beta(2)- and beta(3)-amino acids

Lin, Weilong and Zhang, Ke-Feng and Baudoin, Olivier. (2019) Regiodivergent enantioselective C-H functionalization of Boc-1,3-oxazinanes for the synthesis of beta(2)- and beta(3)-amino acids. Nature Catalysis , 2 (10). pp. 882-888.

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Abstract

beta(2)- and beta(3)-amino acids are important chiral building blocks for the design of new pharmaceuticals and peptidomimetics. Here, we report a straightforward regio- and enantiodivergent access to these compounds using a one-pot reaction composed of sparteine-mediated enantioselective lithiation of a Boc-1,3-oxazinane, transmetallation to zinc and direct or migratory Negishi coupling with an organic electrophile. The regioselectivity of the Negishi coupling was highly ligand-controlled and switch-able to obtain the C4- or the C5-functionalized product exclusively. High enantioselectivities were achieved on a broad range of examples, and a catalytic version in chiral diamine was developed using the (+)-sparteine surrogate. Selected C4- and C5-functionalized Boc-1,3-oxazinanes were subsequently converted to highly enantioenriched beta(2)- and beta(3)-amino acids with the (R) or (S) configuration, depending on the sparteine enantiomer employed in the lithiation step.
Faculties and Departments:05 Faculty of Science > Departement Chemie > Chemie > Synthetische Chemie (Baudoin)
UniBasel Contributors:Baudoin, Olivier
Item Type:Article, refereed
Article Subtype:Research Article
Publisher:Springer Nature
e-ISSN:2520-1158
Note:Publication type according to Uni Basel Research Database: Journal article
Language:English
Identification Number:
Last Modified:30 Oct 2019 15:17
Deposited On:30 Oct 2019 15:17

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