Highly diastereoselective synthesis of enantioenriched: Anti -α-allyl-β-fluoroamines

Highly diastereoselective synthesis of enantioenriched: Anti -α-allyl-β-fluoroamines

© 2019 The Royal Society of Chemistry. 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 ov...

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Bibliographic Details
Main Authors: Philip J. Chevis, Sirilak Wangngae, Thanaphat Thaima, Anthony W. Carroll, Anthony C. Willis, Mookda Pattarawarapan, Stephen G. Pyne
Format: Journal
Published: 2019
Subjects:
Chemical Engineering
Chemistry
Materials Science
Online Access:https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=85066149303&origin=inward
http://cmuir.cmu.ac.th/jspui/handle/6653943832/65466
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Institution: Chiang Mai University
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Summary:© 2019 The Royal Society of Chemistry. 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.

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