对映体富集的反式-α-烯丙基-β-氟胺的高非对映选择性合成。

Highly diastereoselective synthesis of enantioenriched anti-α-allyl-β-fluoroamines.

作者信息

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

机构信息

School of Chemistry and Molecular Biosciences, University of Wollongong, Wollongong, New South Wales 2522, Australia.

Research School of Chemistry, Australian National University, Canberra, ACT 0200, Australia.

出版信息

Chem Commun (Camb). 2019 May 28;55(43):6050-6053. doi: 10.1039/c9cc02765c. Epub 2019 May 8.

DOI:10.1039/c9cc02765c

PMID:31065637

Abstract

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.

摘要

已开发出一种高度非对映选择性合成反式-α-烯丙基-β-氟胺的方法，该方法包括醛的对映选择性α-氟化反应，随后进行非对映选择性Petasis烯丙基硼基-曼尼希反应。这两步反应通常能以良好的总收率得到产物，非对映体比例为97∶3至99∶1，对映体过量为86% - 92%。选定的产物被转化为3元、5元和6元环杂环化合物，后两种类型含有环外氟原子。