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Highly diastereoselective synthesis of enantioenriched anti-alpha-allyl-beta-fluoroamines

Chevis, Philip J.; Wangngae, Sirilak; Thaima, Thanaphat; Carroll, Anthony W; Willis, Anthony; Pattarawarapan, Mookda; Pyne, Stephen G

Description

A highly diastereoselective synthesis of anti-α-allyl-β-fluoroamines has been developed involving enantioselective α-fluorination of aldehydes followed by a diastereoselective Petasis allyl borono-Mannich reaction. The products are obtained generally in good overall yields for the two steps and with drs of 97 : 3–99 : 1 and ees of 86–92%. Selected products were converted to 3-, 5- and 6-membered ring heterocycles, the latter two types incorporating an exo-cyclic fluorine.

CollectionsANU Research Publications
Date published: 2019
Type: Journal article
URI: http://hdl.handle.net/1885/201683
Source: Chemical Communications
DOI: 10.1039/c9cc02765c

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