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Asymmetric allylic alkylation of Morita-Baylis-Hillman carbonates with ?-fluoro-?-keto esters.

ABSTRACT: In the presence of a commercially available Cinchona alkaloid as catalyst, the asymmetric allylic alkylation of Morita-Baylis-Hillman carbonates, with ?-fluoro-?-keto esters as nucleophiles, have been successfully developed. A series of important fluorinated adducts, with chiral quaternary carbon centres containing a fluorine atom, was achieved in good yields (up to 93%), with good to excellent enantioselectivities (up to 96% ee) and moderate diastereoselectivities (up to 4:1 dr).

SUBMITTER: Yan L

PROVIDER: S-EPMC3778419 | biostudies-literature | 2013

REPOSITORIES: biostudies-literature

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Asymmetric allylic alkylation of Morita-Baylis-Hillman carbonates with α-fluoro-β-keto esters.

Yan Lin L Han Zhiqiang Z Zhu Bo B Yang Caiyun C Tan Choon-Hong CH Jiang Zhiyong Z

Beilstein journal of organic chemistry 20130911

In the presence of a commercially available Cinchona alkaloid as catalyst, the asymmetric allylic alkylation of Morita-Baylis-Hillman carbonates, with α-fluoro-β-keto esters as nucleophiles, have been successfully developed. A series of important fluorinated adducts, with chiral quaternary carbon centres containing a fluorine atom, was achieved in good yields (up to 93%), with good to excellent enantioselectivities (up to 96% ee) and moderate diastereoselectivities (up to 4:1 dr). ...[more]

PMID: 24062852

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